[ CAS No. 112-47-0 ] {[proInfo.proName]}

Name: 112-47-0|1,10-Decanediol|97%
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Product Details of [ 112-47-0 ]

CAS No. :	112-47-0	MDL No. :	MFCD00004749
Formula :	C₁₀H₂₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FOTKYAAJKYLFFN-UHFFFAOYSA-N
M.W :	174.28	Pubchem ID :	37153
Synonyms :

Calculated chemistry of [ 112-47-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	9
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	52.51
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.6 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.65
Log Po/w (XLOGP3) :	2.49
Log Po/w (WLOGP) :	2.09
Log Po/w (MLOGP) :	1.91
Log Po/w (SILICOS-IT) :	2.48
Consensus Log Po/w :	2.32

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.9
Solubility :	2.22 mg/ml ; 0.0127 mol/l
Class :	Very soluble
Log S (Ali) :	-2.98
Solubility :	0.181 mg/ml ; 0.00104 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.77
Solubility :	0.293 mg/ml ; 0.00168 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.68

Safety of [ 112-47-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 112-47-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 112-47-0 ]
Downstream synthetic route of [ 112-47-0 ]

[ 112-47-0 ] Synthesis Path-Upstream 1~16

1
[ 112-47-0 ]
[ 4101-68-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrogen bromide In octane; water at 145℃; for 7 h; Dean-Stark	General procedure: A one-neck rb flask was charged with diol (1equiv), 48percent aq HBr (~3 equiv/OH), octane (~7:1 v/w ratio vs diol), fitted tothe fractionating column/Dean-Stark trap, and heated inan oil bath (145-150 °C) w/rapid magnetic stirring. The aqueous (lower) layer of the initialazeotrope condensate (bp 89-92 °C) was tapped offuntil about half of the theoretical amount of H₂O had been collected;the azeotrope temp (still head) then began to rise. The condenser was set to total reflux forseveral h, reopened, and aq material collected for 1h more (head temp 96-100°C). The final volume of aq distillatewas 90-100+percent of theory (higher-boiling distillate contained up to 24percent HBr). When the (pale tan) octane phase containedboth dibromide and bromoalkanol (6band 6c), washing with cold 85percent v/v H₂SO₄ (10 mL,then 5 mL) removed all color and all bromoalkanol. For all three dibromides (3b, 4b, 6b) the neutralized octane solutionwas stripped of solvent (vigreux column, reduced pressure), and the essentiallypure residue (¹H NMR) was kugelrohr distilled. A trace of 4-methyltetrahydropyran was foundin 4b before distillation.

Reference： [1] Tetrahedron Letters, 2015, vol. 56, # 4, p. 630 - 632
[2] Green Chemistry, 2014, vol. 16, # 2, p. 836 - 843
[3] Journal of Organic Chemistry, 2015, vol. 80, # 11, p. 5386 - 5394
[4] Journal of the American Chemical Society, 1936, vol. 58, p. 488
[5] Journal of the Chemical Society, 1958, p. 2068
[6] Monatshefte fuer Chemie, 1910, vol. 31, p. 181
[7] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1910, vol. 42, p. 1658[8] Chem. Zentralbl., 1911, vol. 82, # I, p. 1500
[9] Helvetica Chimica Acta, 1926, vol. 9, p. 265
[10] Journal of the American Chemical Society, 1930, vol. 52, p. 5281
[11] Organic Syntheses, 1940, vol. 20, p. 24
[12] Synthesis, 1987, # 5, p. 511 - 512

2
[ 112-47-0 ]
[ 53463-68-6 ]
[ 4101-68-2 ]

Reference： [1] Tetrahedron, 1998, vol. 54, # 27, p. 7735 - 7748
[2] Journal of Organic Chemistry, 2000, vol. 65, # 18, p. 5837 - 5838
[3] Tetrahedron, 2009, vol. 65, # 20, p. 3961 - 3966
[4] Tetrahedron, 2004, vol. 60, # 24, p. 5237 - 5252
[5] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1215 - 1220
[6] Organic Process Research and Development, 2011, vol. 15, # 3, p. 673 - 680
[7] Helvetica Chimica Acta, 1926, vol. 9, p. 226
[8] Tetrahedron Letters, 2015, vol. 56, # 4, p. 630 - 632

3
[ 112-47-0 ]
[ 497-19-8 ]
[ 4101-68-2 ]

Yield	Reaction Conditions	Operation in experiment
95 wt. %	With concentrated aqueous HBr In water; chlorobenzene	EXAMPLE I A 5 liter jacketed 3-necked round bottom flask was equipped with a mechanical stirrer, a reflux condenser, and an addition funnel. A quantity of 768 grams (1086 milliliters, 8.4 mole) of concentrated aqueous HBr (48 wt. percent) was placed in the reactor, followed by 696 g (4 mol) of 1,10-decanediol. 940 grams (532 milliliters, 8.4 mole) of concentrated H2 SO4 (96 wt. percent) was then added dropwise over several minutes. Steam was then introduced through the vessel jacket, raising the temperature of the reaction contents to about 100°-105° C. Steam was applied for about five hours, the reactor allowed to cool for about thirty minutes, then 2 L of water added, stirred briefly and allowed to stand overnight. The aqueous layer was decanted and the reactor contents then washed with about 2 L of saturated sodium bicarbonate solution. If necessary to assure neutral or slightly basic pH, Na2 CO3 was added. Optionally, about 300-500 mL of chlorobenzene could be added to aid emulsion breaking. The aqueous layer was discarded and the organic layer distilled to recover dibromide product boiling at 159°-163° C. at; 5-6 mm Hg. A 54 mol percent yield (640 g) of 1,10-dibromodecane (>95 wt. percent purity) was obtained.

Reference： [1] Patent: US4540826, 1985, A,

4
[ 112-47-0 ]
[ 4101-68-2 ]

Reference： [1] Patent: US4540826, 1985, A,

5
[ 112-47-0 ]
[ 13019-22-2 ]
[ 4101-68-2 ]

Reference： [1] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1215 - 1220

6
[ 112-47-0 ]
[ 10035-10-6 ]
[ 4101-68-2 ]

Reference： [1] Monatshefte fuer Chemie, 1910, vol. 31, p. 181

7
[ 112-47-0 ]
[ 10035-10-6 ]
[ 856380-74-0 ]
[ 4101-68-2 ]

Reference： [1] Helvetica Chimica Acta, 1946, vol. 29, p. 1204,1207

8
[ 112-47-0 ]
[ 646-25-3 ]

Reference： [1] Chem. Zentralbl., 1937, vol. 108, # II, p. 857
[2] Patent: US2078922, 1934, ,
[3] Patent: US2412209, 1943, ,
[4] Chem.Abstr., 1947, p. 1237
[5] Patent: US2012/232292, 2012, A1, . Location in patent: Page/Page column 10; 13
[6] Angewandte Chemie - International Edition, 2012, vol. 51, # 36, p. 9156 - 9159[7] Angew. Chem., 2012, vol. 124, # 36, p. 9290 - 9293
[8] Patent: JP5808437, 2015, B2, . Location in patent: Paragraph 0099; 0113
[9] Patent: CN103502212, 2016, B, . Location in patent: Paragraph 0207-0208; 0214
[10] Patent: US2412209, 1943, ,
[11] Patent: US2078922, 1934, ,

9
[ 112-47-0 ]
[ 23160-46-5 ]
[ 646-25-3 ]

Reference： [1] Patent: US2012/232293, 2012, A1, . Location in patent: Page/Page column 12; 16
[2] Patent: US2012/232294, 2012, A1, . Location in patent: Page/Page column 13-14; 19
[3] Patent: US2012/232292, 2012, A1, . Location in patent: Page/Page column 10; 13
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 36, p. 9156 - 9159[5] Angew. Chem., 2012, vol. 124, # 36, p. 9290 - 9293
[6] Patent: JP2016/27052, 2016, A, . Location in patent: Paragraph 0088; 0103
[7] Green Chemistry, 2018, vol. 20, # 20, p. 4591 - 4595

10
[ 112-47-0 ]
[ 53463-68-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With hydrogen bromide In water; toluene for 16 h; Inert atmosphere; Reflux; Dean-Stark	1,10-Decanediol 15 (10 g, 57.47 mmol) in toluene (600 mL) was taken in a 1 L two-neck round bottom flask equipped with a Dean Stark apparatus, to which HBr (48percent, 7.15 mL, 63.21 mmol) was added and refluxed for 16 h. After cooling, the reaction mixture was washed with 1 N HCl, 2 M aq NaOH, H₂O, and brine. The organic layer was dried over Na₂SO₄, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (15percent EtOAc/hexanes) to give bromo-alcohol as a clear oil (12.7 g, 93percent). R_f=0.45 (20percent EtOAc/hexanes); ¹H NMR (500 MHz, CDCl₃): δ 3.63 (t, J=5.8 Hz, 2H), 3.39 (t, J=6.8 Hz, 2H), 1.85 (m, 2H), 1.56 (m, 2H), 1.42 (m, 2H), 1.38–1.27 (m, 10H); ¹³C NMR (125 MHz, CDCl₃): δ 62.9, 33.9, 32.7, 32.6, 29.3, 29.2, 29.2, 28.6, 28.0, 25.6; IR (neat): ν_max 2927, 2856, 1738, 1593, 1449, 1367, 1241 cm⁻¹; HRMS (ESI) calcd for C₁₀H₂₂BrO [M+H]⁺ 237.0854, found 237.0845.
92%	With hydrogen bromide In toluene at 180℃; for 24 h;	To a solution of 1,10-decandiol (3) (34.8 g, 0.2 mol, 1 equiv) in toluene (400 mL) was added 48percent HBr (22.6 mL, 0.2 mol, 1 equiv) dropwise with stirring and refluxed at 180 °C using Dean-Stark trap for 24 h. The mixture was cooled to room temperature and washed with 6 N NaOH (150 mL), 10percent HCl (150 mL), H₂O (2 x 250 mL) and brine (200 mL). The organic layer was dried over Na₂SO₄, concentrated and chromatographed on silica gel eluting with cyclohexane/ethylacetate (4:1) to give 43.5 g (92percent) of 10-bromo-1-decanol as a colourless liquid. ¹H NMR δ 3.65 (t, J = 6.7 Hz, 2H, H-1), 3.43 (t, J = 7.0 Hz, 2H, H-10), 1.87 (m, 2H, H-9), 1.57 (m, 2H, H-2), 1.43 (m, 2H, H-3), 1.26-1.41 (m, 10H, H-4-8). ¹³C NMR δ 63.0 (C1), 34.1 (C10), 32.8, 32.6, 29.5, 29.4, 29.3, 28.6, 28.2, 25.6.To a solution of 10-bromo-1-decanol (41 g, 0.17 mol, 1 equiv) in 130 mL of acetone at -5 °C was added slowly chromic acid solution prepared from CrO₃ (25.7 g, 0.26 mol, 1.5 equiv), water (25 mL) and conc H₂SO₄ (22.5 mL, 0.34 mol, 2 equiv) at 0 °C, then stirred for 2 h and left over night at room temperature. The mixture was extracted with diethyl ether (3 x 250 mL), washed with water (250 mL) and brine (250 mL), dried over Na₂SO₄ and concentrated. The residue was chromatographed on silica gel eluting with CH₂Cl₂ afforded 31.0 g of 10-bromodecanoic acid (4d) (73percent) as a white solid after recrystallization from petroleum ether.
90%	With hydrogen bromide In water; toluene for 72 h; Heating / reflux	EXAMPLE 1 To a mixture of 1,10-decanediol (35.73g, 0.205 mol) and toluene (700 mL) was added concentrated HBr (29 mL of 47percent aqueous solution, 0.24 mol). The heterogeneous mixture was stirred and heated at reflux for 36 hours. TLC analysis indicated substantial amounts of 1,10-decanediol still remained. Thus a further quantity of HBr (15 mL, 0.12 mol) was added and the mixture was heated at reflux for further 36 h, at which time TLC analysis showed no diol remaining. The reaction mixture was allowed to cool to room temperature and the phases were separated. The organic layer was concentrated by evaporating the toluene and diluted with ethyl acetate and washed with water, sodium bicarbonate and brine. Then the organic layer was dried over Na₂SO₄ and concentrated to yellow liquid and purification of this crude reaction mixture by column chromatography provided pure 10-bromodecanol (43.0 g) in 90percent yield.

90%	With hydrogen bromide In water; toluene for 72 h; Heating / reflux	EXAMPLE 1 To a mixture of 1,10-decanediol (35.73g, 0.205 mol) and toluene (700 mL) was added concentrated HBr (29 mL of 47percent aqueous solution, 0.24 mol). The heterogeneous mixture was stirred and heated at reflux for 36 hours. TLC analysis indicated substantial amounts of 1,10-decanediol still remained. Thus a further quantity of HBr (15 mL, 0.12 mol) was added and the mixture was heated at reflux for further 36 h, at which time TLC analysis showed no diol remaining. The reaction mixture was allowed to cool to room temperature and the phases were separated. The organic layer was concentrated by evaporating the toluene and diluted with ethyl acetate and washed with water, sodium bicarbonate and brine. Then the organic layer was dried over Na₂SO₄ and concentrated to yellow liquid and purification of this crude reaction mixture by column chromatography provided pure 10-bromodecanol (43.0 g) in 90percent yield.
89%	With hydrogen bromide In cyclohexane; water for 6 h; Heating / reflux	Synthesis Example A-(1) 1,10-Decanediol (4 g) was dissolved in 100 ml of cyclohexane, and 57percent aqueous hydrobromic acid solution (58 ml) was added to this solution. The reaction mixture was refluxed for six hours while stirring. After the reaction, the mixture was extracted three times with diethyl ether. The organic layer was neutralized with saturated sodium hydrogen carbonate solution, washed with saline solution, dried over magnesium sulfate, and filtered, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel flash chromatography (hexane: ethyl acetate = 7:3) gave 10-bromodecan-1-ol as white crystals at an 89percent yield. Molecular weight: 237.18 (C₁₀H₂₁BrO) TLC: (hexane-ethyl acetate=7-3) Rf value: 0.53 ¹H-NMR: (300MHz, CDCl₃)δ: 1.26 (s large, 12H, -(CH₂)₆-); 1.56 (qt, 2H, J=7.0Hz, -CH₂-); 1.85 (qt, 2H, J=7.1Hz, -CH₂-); 3.40 (t, 2H, J=6.9Hz, -CH₂-Br); 3.64 (t, 2H, J=6.6Hz, -CH₂-O-) ¹³C-NMR: (75MHz, CDCl₃) δ: 25.70; 28.14-29.45; 32.77; 32.80; 34.03; 63.05
80%	With hydrogen bromide; tetra-(n-butyl)ammonium iodide In water for 0.0833333 h; Microwave irradiation	A mixture of 1, 10-decanediol (0.3 g, 1.72mmol), 48percent aq. hydrogen bromide (0.29 g, 3.58 mmol) and tetrabutylammonium iodide (0.12 g, 0.34 mmol) was subjected to MWI at 355 W for 5 min. The reaction mixture was cooled, extracted with diethyl ether (3x10 mL) and washed with saturated sodium bicarbonate solution (2 x 5 mL), 10percent aq. sodium thiosulfate (2 x 5 mL), water (2 x5 mL), and brine and dried. The evaporation of solvent under reduced pressure furnished the crude product, which was purified by column chromatography over silica gel using 5percent ethyl acetate in n-hexane to afford pure product (3, 0.32 g, 80percent) as a colourless oil.
73%	With hydrogen bromide In water; toluene for 16 h; Reflux	HBr (48percent in H2O, w/w, 16.3 mL, 138 mmol) was added to a mixture ofdecane-1,10-diol (2; 20 g, 115 mmol) and toluene (250 mL). The resultingmixture was stirred at reflux temperature for 16 h. Afterreaching r.t. and careful addition of sat. aq Na2S2O3 (50 mL), the aqueouslayer was extracted with EtOAc (3 × 200 mL). The combined extractswere dried (MgSO4), filtered, and the solvent was evaporated.Purification of the residue by flash chromatography (silica gel, hexanes/EtOAc, 4:1 to 2:1) afforded the title compound as a colorless oil(19.8 g, 73percent).IR (ATR): 3328, 2924, 2853, 1463, 1437, 1371, 1352, 1256, 1242, 1129,1055, 899, 756, 722, 644, 562, 505, 465, 445, 428, 417 cm–1.1H NMR (400 MHz, CDCl3): δ = 3.63 (t, J = 6.6 Hz, 2 H), 3.40 (t, J = 6.9Hz, 2 H), 1.88–1.80 (m, 2 H), 1.60–1.51 (m, 2 H), 1.46–1.24 (m, 13 H).13C NMR (100 MHz, CDCl3): δ = 63.2, 34.2, 32.92, 32.89, 29.6, 29.49,29.48, 28.9, 28.3, 25.8.HRMS-ESI: m/z calcd for [C10H21BrO + Na]+: 259.0669; found:259.0668.
59%	With hydrogen bromide In toluene at 20℃; for 18 h;	adding toluene 500 ml in a 1 L three-necked flask, 1 175g of 10-decanediol, adding 200ml of 40percent hydrobromic acid, stirring at room temperature for 18h, separating the liquid, washing the toluene phase with 200ml saturated laboratory, drying, concentrated crude product 240g,Column chromatography (EA: PE = 4:1) gave 140 g of 10-bromofurfuryl alcohol in a yield of 59percent

Reference： [1] Tetrahedron, 2015, vol. 71, # 7, p. 1058 - 1067
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 3, p. 1083 - 1092
[3] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 6, p. 273 - 276
[4] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579
[5] Patent: EP1818336, 2007, A1, . Location in patent: Page/Page column 7
[6] Patent: US2007/191606, 2007, A1, . Location in patent: Page/Page column 4-5
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[8] Patent: EP1854777, 2007, A1, . Location in patent: Page/Page column 12
[9] Patent: EP1102775, 2005, B1, . Location in patent: Page/Page column 10
[10] Tetrahedron, 1992, vol. 48, # 16, p. 3413 - 3428
[11] Chemical Research in Toxicology, 2012, vol. 25, # 10, p. 2253 - 2260
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[14] Organic Letters, 2015, vol. 17, # 21, p. 5248 - 5251
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[22] Journal of Organic Chemistry, 1986, vol. 51, # 2, p. 260 - 263
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[41] Tetrahedron Letters, 1989, vol. 30, # 15, p. 1991 - 1992
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[57] Langmuir, 2015, vol. 31, # 39, p. 10831 - 10842

11
[ 112-47-0 ]
[ 53463-68-6 ]
[ 4101-68-2 ]

12
[ 112-47-0 ]
[ 2162-98-3 ]

Reference： [1] Russian Journal of Bioorganic Chemistry, 2002, vol. 28, # 1, p. 62 - 64
[2] Journal of Organic Chemistry, 1953, vol. 18, p. 728,731,733
[3] Journal of the American Chemical Society, 1951, vol. 73, p. 2730,2731
[4] Pharmaceutical Chemistry Journal, 1972, vol. 6, # 5, p. 283 - 286[5] Khimiko-Farmatsevticheskii Zhurnal, 1972, vol. 6, # 5, p. 11 - 14
[6] Scientific Papers of the Institute of Physical and Chemical Research (Japan), p. 13[7] Chem. Zentralbl., 1931, vol. 102, # II, p. 1694
[8] Synthetic Communications, 2001, vol. 31, # 3, p. 367 - 373

13
[ 112-47-0 ]
[ 51309-10-5 ]
[ 2162-98-3 ]

Reference： [1] Chemistry of Natural Compounds, 1994, vol. 30, # 1, p. 121 - 123[2] Khimiya Prirodnykh Soedinenii, 1994, # 1, p. 130 - 132

14
[ 7719-09-7 ]
[ 112-47-0 ]
[ 2162-98-3 ]

Reference： [1] Scientific Papers of the Institute of Physical and Chemical Research (Japan), vol. 16, p. 13[2] Chem. Zentralbl., 1931, vol. 102, # II, p. 1694

15
[ 112-47-0 ]
[ 50530-12-6 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539
[2] Journal of the American Chemical Society, 1956, vol. 78, p. 2255,2256[3] Journal of Organic Chemistry, 1956, vol. 21, p. 883,885
[4] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579

16
[ 112-47-0 ]
[ 85590-00-7 ]

Reference： [1] Patent: CN104151350, 2016, B,

[ 112-47-0 ] Synthesis Path-Downstream 1~88

1
[ 112-47-0 ]
[ 542-52-9 ]
[ 67990-00-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium Erhitzen des Reaktionsprodukts unter 0.5 Torr auf 250grad;
	With tin(ll) chloride at 200℃; Erhitzen des Reaktionsprodukts mit wenig Zinn(II)-chlorid unter 1 Torr auf 268grad;
	With sodium Erhitzen des Reaktionsprodukts unter 0.5 Torr auf 250grad;

Reference： [1]Hill; Carothers [Journal of the American Chemical Society, 1933, vol. 55, p. 5031,5034]
[2]Current Patent Assignee: Du Pont de Nemours & Co. - US2092031, 1935, A
[3]Current Patent Assignee: DUPONT DE NEMOURS INC - DE690629, 1934, C Current Patent Assignee: Du Pont de Nemours & Co. - US2020298, 1933, A [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.]

2
[ 112-47-0 ]
[ 871-70-5 ]
1,12-dioxa-cyclotriacontane-13,30-dione [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1935,vol. 57,p. 935

3
[ 112-47-0 ]
[ 102-39-6 ]
1,4,15,18-tetraoxa-[18]metacyclophane-3,16-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 200℃; Erhitzen des Reaktionsgemisches mit Zinn(II)-chlorid-dihydrat unter 1 Torr auf 270grad;

Reference： [1]Spanagel; Carothers [Journal of the American Chemical Society, 1935, vol. 57, p. 935]

4
[ 112-47-0 ]
[ 111-20-6 ]
[ 1679-53-4 ]

Reference： [1],1958,p. 22
Chem.Abstr.,1959,p. 15966

5
[ 112-47-0 ]
[ 51309-10-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With hydrogenchloride In octane; n-heptane; water at 87℃; for 20h;
71%	Stage #1: 1,10-Decanediol With lithium chloride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: With pyridine; methanesulfonyl chloride at 0℃; for 23h;	10-chlorodecan-1-ol (SI-3) LiCl (1.34 g, 31.6 mmol, 1.8 equiv.) was added to a solution of 1,10-decandiol (3.00 g, 17.2 mmol, 1.0 equiv.) in DMF (40 mL) at room temperature, and the mixture was stirred for 10 mins. This mixture was then cooled to 0 °C and pyridine (1.40 g, 17.7 mmol, 1.0 equiv.) and MsCl (0.65 g, 5.7 mmol, 0.3 equiv.) were added. The resulting solution was stirred at room temperature for 23 h, taken up with Et2O (150 mL) and washed with HCl 0.5 M (4 × 150 mL). The organic extract was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (DCM/EtOAc 9:1, Rf = 0.39) to afford 0.78 g, 4.1 mmol of SI-3 (71 % yield) as a colourless oil. 1H NMR (300 MHz, CDCl3) δ 3.62 (t, J = 6.6 Hz, 2H, -CH2-OH), 3.52 (t, J = 6.7 Hz, 2H, -CH2-Cl), 1.82-1.69 (m, 2H, -CH2-CH2-Cl), 1.61-1.47 (m, 3H, -CH2-CH2-OH and -OH), 1.47-1.22 (m, 12H, 6 × -CH2). 13C NMR (75 MHz, CDCl3) δ 63.0, 45.2, 32.8, 32.7, 29.5, 29.5, 28.9, 26.9, 25.8.
60%	With hydrogenchloride In water; toluene for 9h; Heating;

	With hydrogenchloride
	With hydrogenchloride; water
	With hydrogenchloride
	With tetrachloromethane; triphenylphosphine In dichloromethane for 48h; Reflux;

Reference： [1]Karpinska; Lewandowska; Grodner [Polish Journal of Chemistry, 2004, vol. 78, # 7, p. 937 - 942]
[2]Mattarei, Andrea; Rossa, Andrea; Bombardelli, Veronica; Azzolini, Michele; La Spina, Martina; Paradisi, Cristina; Zoratti, Mario; Biasutto, Lucia [European Journal of Medicinal Chemistry, 2017, vol. 135, p. 77 - 88]
[3]Kovalev, B. G.; Matveeva, E. D.; Stan, V. V.; Vovk, G. A.; Yudin, L. G.; Kost, A. N. [Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, # 10, p. 1728 - 1733][Zhurnal Organicheskoi Khimii, 1980, vol. 16, # 10, p. 2032 - 2038]
[4]Bennett; Mosses [Journal of the Chemical Society, 1931, p. 1699]
[5]Pattison et al. [Journal of Organic Chemistry, 1956, vol. 21, p. 739,743,746][Journal of the American Chemical Society, 1956, vol. 78, p. 3484,3485]
[6]Alberti; Smiecinszewski [Monatshefte fur Chemie, 1906, vol. 27, p. 412]
[7]Iwasaki, Takanori; Terahigashi, Shohei; Wang, Yufei; Tanaka, Arisa; Zhao, Hanqing; Fujimoto, Yukari; Fukase, Koichi; Kambe, Nobuaki [Advanced Synthesis and Catalysis, 2018, vol. 360, # 19, p. 3810 - 3817]

6
[ 112-47-0 ]
[ 646-25-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia;(carbonyl)chloro(hydrido)tris(triphenylphosphine)ruthenium(II); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine]; In toluene; at 180℃; under 32253.2 Torr; for 24h;Inert atmosphere;Product distribution / selectivity;	Ligand L, metal salt M, solvent and the stated alcohol were introduced as initial charge under an Ar atmosphere in a 160 ml Parr autoclave (hte, (stainless steel V4A)) with magnetically coupled slanted-blade stirrer (stirring speed: 200-500 revolutions/minute). The stated amount of ammonia was either precondensed at room temperature or directly metered in from the NH3 pressurized-gas bottle. If hydrogen was used, this was carried out by means of iterative differential pressure metering. The steel autoclave was heated electrically up to the stated temperature and heated (internal temperature measurement) for the stated time with stirring (500 revolutions/minute). After cooling to room temperature, decompressing the autoclave and outgassing the ammonia at atmospheric pressure, the reaction mixture was analyzed by means of GC (30 m RTX5 amine 0.32 mm 1.5 mum). Purification of the particular product can be carried out, for example, by distillation. The results for the amination of octanol (Table 1a and 1b), 1,4-butanediol (Table 2), diethylene glycol (Table 3), 1,9-nonanediol, 1,6-hexanediol, 1,10-decandiol (Table 4) and 1,2-dimethanolfuran (Table 5) are given below:
	With chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II); ammonia; In toluene; at 155℃; under 33228.3 Torr; for 12h;Autoclave; Inert atmosphere;	General procedure: Example General Rules on the catalyst amination of alcohol with ammoniaaccording to the present invention (See below for manufacturing, initialweighed under an inert atmosphere) catalyst complex XIVb and, with the solvent(amount of up to solvent total amount reaches the 50ml), and the alcohol thatthe reaction is, under an argon atmosphere, magnetic coupling type tilt wingsParr autoclave of 160ml equipped with a stirrer (made of special steel V4A)(stirring speed: 200 to 500 rev / min) were charged in. At described the amountof ammonia at room temperature, it has been directly metered from thepreliminary condensed with or NH 3 gas cylinder. If hydrogen is used, this wasdone by repeated differential-pressure volume. Steel autoclave is electricheating heated to the temperature indicated, for a period of time described, ithas been heated under stirring (500 rev / min) (internal temperaturemeasurement). The autoclave was cooled to room temperature, depressurized,after performing outgassing of ammonia at atmospheric pressure, the reactionmixture was analyzed by GC (30m RTX5 Amin 0.32mm, 1.5mum). The desired product,for example, can be isolated by distillation
	With (carbonyl)chloro(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 180℃; under 32253.2 Torr; for 24h;Autoclave; Inert atmosphere;	General procedure: The ligand L, the metal salt M, the solvent and the alcohol were introduced as an initial feed into a 160 ml Parr autoclave (hte) having a magnetically coupled tilt blade stirrer (stirring rate: 200 to 500 rpm) in an Ar atmosphere , (Stainless steel V4A)). The amount of ammonia is pre-concentrated at room temperature or directly from a cylinder pressurized with NH3. If hydrogen is used, this is done by adding a repeated differential pressure differential. The steel autoclave was electrically heated to the temperature and heated for the time (internal temperature measurement) with stirring (500 revolutions per minute). After cooling to room temperature, the autoclave was decompressed and ammonia was withdrawn at atmospheric pressure, and the reaction mixture (30 m RTX5 amine 0.32 mml. 5 [mu] [pi]) was analyzed by GC. Purification of a specific product can be carried out, for example, by distillation. Octyl alcohol (Table 1), 1,9-nonanediol, 1,6-hexanediol, 1,10_ The amination results of diols (Table 4) and 2,5-dimethanolfuran (Table 5) are given below.

Reference： [1]Chemisches Zentralblatt,1937,vol. 108,p. 857
[2]Chemical Abstracts,1947,p. 1237
[3]Patent: US2012/232292,2012,A1 .Location in patent: Page/Page column 10; 13
[4]Angewandte Chemie - International Edition,2012,vol. 51,p. 9156 - 9159
Angew. Chem.,2012,vol. 124,p. 9290 - 9293
[5]Patent: JP5808437,2015,B2 .Location in patent: Paragraph 0099; 0113
[6]Patent: CN103502212,2016,B .Location in patent: Paragraph 0207-0208; 0214
[7]Patent: US2412209,1943,
[8]Patent: US2078922,1934,

7
[ 112-47-0 ]
[ 53463-68-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With hydrogen bromide In water; toluene for 16h; Inert atmosphere; Reflux; Dean-Stark;	4.2 2-((10-Bromodecyl)oxy)tetrahydro-2H-pyran (16) 1,10-Decanediol 15 (10 g, 57.47 mmol) in toluene (600 mL) was taken in a 1 L two-neck round bottom flask equipped with a Dean Stark apparatus, to which HBr (48%, 7.15 mL, 63.21 mmol) was added and refluxed for 16 h. After cooling, the reaction mixture was washed with 1 N HCl, 2 M aq NaOH, H2O, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (15% EtOAc/hexanes) to give bromo-alcohol as a clear oil (12.7 g, 93%). Rf=0.45 (20% EtOAc/hexanes); 1H NMR (500 MHz, CDCl3): δ 3.63 (t, J=5.8 Hz, 2H), 3.39 (t, J=6.8 Hz, 2H), 1.85 (m, 2H), 1.56 (m, 2H), 1.42 (m, 2H), 1.38-1.27 (m, 10H); 13C NMR (125 MHz, CDCl3): δ 62.9, 33.9, 32.7, 32.6, 29.3, 29.2, 29.2, 28.6, 28.0, 25.6; IR (neat): νmax 2927, 2856, 1738, 1593, 1449, 1367, 1241 cm-1; HRMS (ESI) calcd for C10H22BrO [M+H]+ 237.0854, found 237.0845.
92%	With hydrogen bromide In water; toluene Reflux; Inert atmosphere;
92%	With hydrogen bromide In water; toluene Reflux;

92%	With hydrogen bromide In toluene at 180℃; for 24h;	3.2.3. Synthesis of 10-bromodecanoic acid (4d) To a solution of 1,10-decandiol (3) (34.8 g, 0.2 mol, 1 equiv) in toluene (400 mL) was added 48% HBr (22.6 mL, 0.2 mol, 1 equiv) dropwise with stirring and refluxed at 180 °C using Dean-Stark trap for 24 h. The mixture was cooled to room temperature and washed with 6 N NaOH (150 mL), 10% HCl (150 mL), H2O (2 x 250 mL) and brine (200 mL). The organic layer was dried over Na2SO4, concentrated and chromatographed on silica gel eluting with cyclohexane/ethylacetate (4:1) to give 43.5 g (92%) of 10-bromo-1-decanol as a colourless liquid. 1H NMR δ 3.65 (t, J = 6.7 Hz, 2H, H-1), 3.43 (t, J = 7.0 Hz, 2H, H-10), 1.87 (m, 2H, H-9), 1.57 (m, 2H, H-2), 1.43 (m, 2H, H-3), 1.26-1.41 (m, 10H, H-4-8). 13C NMR δ 63.0 (C1), 34.1 (C10), 32.8, 32.6, 29.5, 29.4, 29.3, 28.6, 28.2, 25.6.To a solution of 10-bromo-1-decanol (41 g, 0.17 mol, 1 equiv) in 130 mL of acetone at -5 °C was added slowly chromic acid solution prepared from CrO3 (25.7 g, 0.26 mol, 1.5 equiv), water (25 mL) and conc H2SO4 (22.5 mL, 0.34 mol, 2 equiv) at 0 °C, then stirred for 2 h and left over night at room temperature. The mixture was extracted with diethyl ether (3 x 250 mL), washed with water (250 mL) and brine (250 mL), dried over Na2SO4 and concentrated. The residue was chromatographed on silica gel eluting with CH2Cl2 afforded 31.0 g of 10-bromodecanoic acid (4d) (73%) as a white solid after recrystallization from petroleum ether.
90%	With hydrogen bromide In water; toluene for 72h; Heating / reflux;	1 EXAMPLE 1 To a mixture of 1,10-decanediol (35.73g, 0.205 mol) and toluene (700 mL) was added concentrated HBr (29 mL of 47% aqueous solution, 0.24 mol). The heterogeneous mixture was stirred and heated at reflux for 36 hours. TLC analysis indicated substantial amounts of 1,10-decanediol still remained. Thus a further quantity of HBr (15 mL, 0.12 mol) was added and the mixture was heated at reflux for further 36 h, at which time TLC analysis showed no diol remaining. The reaction mixture was allowed to cool to room temperature and the phases were separated. The organic layer was concentrated by evaporating the toluene and diluted with ethyl acetate and washed with water, sodium bicarbonate and brine. Then the organic layer was dried over Na2SO4 and concentrated to yellow liquid and purification of this crude reaction mixture by column chromatography provided pure 10-bromodecanol (43.0 g) in 90% yield.
90%	With hydrogen bromide In water; toluene for 72h; Heating / reflux;	1 EXAMPLE 1 To a mixture of 1,10-decanediol (35.73g, 0.205 mol) and toluene (700 mL) was added concentrated HBr (29 mL of 47% aqueous solution, 0.24 mol). The heterogeneous mixture was stirred and heated at reflux for 36 hours. TLC analysis indicated substantial amounts of 1,10-decanediol still remained. Thus a further quantity of HBr (15 mL, 0.12 mol) was added and the mixture was heated at reflux for further 36 h, at which time TLC analysis showed no diol remaining. The reaction mixture was allowed to cool to room temperature and the phases were separated. The organic layer was concentrated by evaporating the toluene and diluted with ethyl acetate and washed with water, sodium bicarbonate and brine. Then the organic layer was dried over Na2SO4 and concentrated to yellow liquid and purification of this crude reaction mixture by column chromatography provided pure 10-bromodecanol (43.0 g) in 90% yield.
89%	With hydrogen bromide In toluene for 16h; Heating;
89%	With hydrogen bromide In cyclohexane; water for 6h; Heating / reflux;	A-1 Synthesis Example A-(1) 1,10-Decanediol (4 g) was dissolved in 100 ml of cyclohexane, and 57% aqueous hydrobromic acid solution (58 ml) was added to this solution. The reaction mixture was refluxed for six hours while stirring. After the reaction, the mixture was extracted three times with diethyl ether. The organic layer was neutralized with saturated sodium hydrogen carbonate solution, washed with saline solution, dried over magnesium sulfate, and filtered, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel flash chromatography (hexane: ethyl acetate = 7:3) gave 10-bromodecan-1-ol as white crystals at an 89% yield. Molecular weight: 237.18 (C10H21BrO) TLC: (hexane-ethyl acetate=7-3) Rf value: 0.53 1H-NMR: (300MHz, CDCl3)δ: 1.26 (s large, 12H, -(CH2)6-); 1.56 (qt, 2H, J=7.0Hz, -CH2-); 1.85 (qt, 2H, J=7.1Hz, -CH2-); 3.40 (t, 2H, J=6.9Hz, -CH2-Br); 3.64 (t, 2H, J=6.6Hz, -CH2-O-) 13C-NMR: (75MHz, CDCl3) δ: 25.70; 28.14-29.45; 32.77; 32.80; 34.03; 63.05
88.93%	With hydrogen bromide In toluene for 24h; Reflux;	Bromodecan-1-ol (8). Decane-1,10-diol (5 g, 28.69 mmol) was dissolved in toluene, 48% aqueous HBr (3.73 mL, 32.99 mmol) was added, and the mixture was refluxed for 24 h. A yellow oily liquid was obtained. Yield 6.12 g (88.93%). 1H NMR spectrum, δ, ppm: 3.80-3.59 m (1H, CH), 1.71-1.54 m (1H, CH), 1.50-1.12 m (4H, CH2), 0.93 d.d (3H, CH2, J = 6.5,4.0 Hz). 13C NMR spectrum, δC, ppm: 61.25 (CH2), 40.01 (CH2), 36.83 (CH2), 29.51 (CH2), 29.20 (CH2), 22.97 (CH2), 19.66 (CH2), 14.11 (CH2).
88.18%	With hydrogen bromide In toluene Reflux;	9 Step (9) Synthesis of 10-bromodecanol Take a 250mL single-mouth bottle, weigh (5g, 28.69mmol, 1eq) 1,10-decanediol, add 125mL of toluene, add HBr (3.73mL, 32.99mmol, 1.15eq, W=48%), connect to a water separator With the condenser, heat to reflux overnight. Point plate detection, no raw material point, wash with saturated sodium bisulfite solution (50mL×3, that is, wash with 50mL saturated sodium bisulfite solution each time, wash 3 times in total), and extract with ethyl acetate (50mL×3, namely Extract with 50 mL of ethyl acetate each time, 3 times in total), combine the organic phases, dry with anhydrous magnesium sulfate, filter with suction, and spin-dried through the column. 6 g of light yellow oily liquid was obtained with a yield of 88.18%.
87%	With hydrogen bromide In water; Petroleum ether for 4h; Heating / reflux;
85%	With hydrogen bromide In benzene for 28h; Heating;
85%	With hydrogen bromide In toluene
84%	With hydrogen bromide In toluene for 72h; Reflux; Inert atmosphere;
84%	With hydrogen bromide In toluene at 110℃; for 24h;	1 Example 1 ynthesis of 10-bromo-1-decanol[0025] Add 1,10-decanediol (321g, 1.712mol), toluene (1000ml), 48% hydrobromic acid in a 2L three-necked bottle(231ml, 2.054mol, 1.2eq), heated to 110C, after reflux for 24 hours, add 48% hydrobromic acid (84ml, 0.753mol,40.44eq), continue heating and refluxing for 24 hours, a small amount of raw material remains detected by gas chromatography. Cool to room temperature and add 500ml of petroleum etherDilute, separate hydrobromic acid, and wash the organic phase with saturated sodium bicarbonate (400ml X 2) and saturated brine (400ml X 2),Dry over anhydrous sodium sulfate. Spin-dry the column to obtain 10-bromo-1-decanol (yield 84%).
82%	With hydrogen bromide In water; toluene at 95 - 97℃; for 72h;
82%	With hydrogen bromide In water; toluene for 48h; Reflux; Inert atmosphere;
81%	With hydrogen bromide
80%	With hydrogen bromide In benzene for 30h; Heating;
80%	With hydrogen bromide In benzene for 28h; Heating;
80%	With hydrogen bromide In benzene Heating;
80%	With tetrabutylammomium bromide; hydrogen bromide In water for 0.0833333h; Microwave irradiation;
80%	With hydrogen bromide; tetra-(n-butyl)ammonium iodide In water for 0.0833333h; Microwave irradiation;	10-Bromodecan-1-ol (3) A mixture of 1, 10-decanediol (0.3 g, 1.72mmol), 48% aq. hydrogen bromide (0.29 g, 3.58 mmol) and tetrabutylammonium iodide (0.12 g, 0.34 mmol) was subjected to MWI at 355 W for 5 min. The reaction mixture was cooled, extracted with diethyl ether (3x10 mL) and washed with saturated sodium bicarbonate solution (2 x 5 mL), 10% aq. sodium thiosulfate (2 x 5 mL), water (2 x5 mL), and brine and dried. The evaporation of solvent under reduced pressure furnished the crude product, which was purified by column chromatography over silica gel using 5% ethyl acetate in n-hexane to afford pure product (3, 0.32 g, 80%) as a colourless oil.
79%	With hydrogen bromide In water; toluene for 43h; Inert atmosphere; Reflux;
78%	With hydrogen bromide at 85℃; for 3h;
78%	With hydrogen bromide
78.5%	With hydrogen bromide In cyclohexane; water at 80℃; for 5h; Inert atmosphere;
77%	With hydrogen bromide In water; toluene for 6h; Reflux;
74%	With hydrogen bromide at 70℃; for 40h;
74.5%	With hydrogen bromide In water; toluene for 36h; Reflux;
74%	With hydrogen bromide In water; toluene for 48h; Reflux;
74%	With hydrogen bromide In water; toluene for 16h; Dean-Stark; Reflux;	2.2.2. Synthesis of 10-bromo-decan-1-ol 2 Hydrobromic acid (1.2 mL 48% aqueous solution, 9.5 mmol) was added to a suspension of 1,10-decanediol 1 (1.5 g, 8.6 mmol) in 30 mL of toluene in a round-bottomed flask equipped with a Dean-Stark trap and a cooler. The mixture was refluxed for 16 h. After cooling, the solvent was removed under reduced pressure. The residue obtained was chromatographed on silica gel using hexane/ethyl acetate (8:2) to yield the pure compound 2 (Scheme 1). Yield 74%; yellow oily product: IR (KBr): v = 3325, 2925, 2850,1450, 1250, 1050, 700, 625, 550 cm-1. 1H NMR (200 MHz, CDCl3): δ1.20-1.40 (m, 12H), 1.45-1.60 (m, 2H), 1.84 (qn, J=6.8 Hz, 2H), 3.39 (t, J=6.8 Hz, 2H), 3.62 (t, J=6.4 Hz, 2H) ppm. 13C NMR (50 MHz, CDCl3) δ: 25.67, 28.11, 28.69, 29, 32, 29.42, 32.73, 32.77, 33.98, 62.99 ppm.
73%	With hydrogen bromide In water; toluene for 16h; Reflux;	10-Bromodecan-1-ol (3) HBr (48% in H2O, w/w, 16.3 mL, 138 mmol) was added to a mixture ofdecane-1,10-diol (2; 20 g, 115 mmol) and toluene (250 mL). The resultingmixture was stirred at reflux temperature for 16 h. Afterreaching r.t. and careful addition of sat. aq Na2S2O3 (50 mL), the aqueouslayer was extracted with EtOAc (3 × 200 mL). The combined extractswere dried (MgSO4), filtered, and the solvent was evaporated.Purification of the residue by flash chromatography (silica gel, hexanes/EtOAc, 4:1 to 2:1) afforded the title compound as a colorless oil(19.8 g, 73%).IR (ATR): 3328, 2924, 2853, 1463, 1437, 1371, 1352, 1256, 1242, 1129,1055, 899, 756, 722, 644, 562, 505, 465, 445, 428, 417 cm-1.1H NMR (400 MHz, CDCl3): δ = 3.63 (t, J = 6.6 Hz, 2 H), 3.40 (t, J = 6.9Hz, 2 H), 1.88-1.80 (m, 2 H), 1.60-1.51 (m, 2 H), 1.46-1.24 (m, 13 H).13C NMR (100 MHz, CDCl3): δ = 63.2, 34.2, 32.92, 32.89, 29.6, 29.49,29.48, 28.9, 28.3, 25.8.HRMS-ESI: m/z calcd for [C10H21BrO + Na]+: 259.0669; found:259.0668.
70%	With hydrogen bromide In n-heptane
70%	With hydrogen bromide In n-heptane for 25h; Heating;
69%	With hydrogen bromide
69%	In hydrogen bromide	XXXV.a 10-Bromodecanol Example XXXVa 10-Bromodecanol A solution of 50 g of decane-1,10-diol in 300 ml of 48% aqueous hydrobromic acid was heated at 90° C. for 24 hours while the solution was extracted continuously with petroleum ether 100-140. After cooling to room temperature, the petroleum ether solution was evaporated and the residue was purified by distillation. Boiling point 121°-124° C. (0.1 mm Hg). Yield 69%. 1H-NMR (CDCl3): 0.98-2.20 ppm, m, 16.0 H (C-(CH2)8 COH); 3.43 ppm, t, J=6.9 Hz, 2.0 H (OCH2); 3.65 ppm, t, J=6.2 Hz, 1.9 H (BrCH2).
68%	With hydrogen bromide In toluene Heating;
67.1%	With hydrogen bromide In ligroin for 72h;
65%	With hydrogen bromide In Petroleum ether at 90 - 95℃; for 65h;
63%	With hydrogen bromide In benzene for 24h; Heating;
59%	With hydrogen bromide In toluene at 20℃; for 18h;	1.1 1). Synthesis of 10-bromononanol (compound b) adding toluene 500 ml in a 1 L three-necked flask, 1 175g of 10-decanediol, adding 200ml of 40% hydrobromic acid, stirring at room temperature for 18h, separating the liquid, washing the toluene phase with 200ml saturated laboratory, drying, concentrated crude product 240g,Column chromatography (EA: PE = 4:1) gave 140 g of 10-bromofurfuryl alcohol in a yield of 59%
57%	With hydrogen bromide In water; toluene for 48h; Reflux; Inert atmosphere;
57%	With hydrogen bromide In water; toluene Reflux; Dean-Stark;
56%	With hydrogen bromide In water; toluene at 90 - 95℃; for 48h;
48%	With hydrogen bromide
	With water; hydrogen bromide
	With hydrogen bromide In n-heptane Heating;
	With hydrogen bromide In Petroleum ether
	With hydrogen bromide In toluene
	With hydrogen bromide In water for 60h; Heating;
	With sulfuric acid; hydrogen bromide for 2h; Heating;
	With hydrogen bromide In n-heptane Heating;
	With hydrogen bromide In cyclohexane for 6h; Heating;
	With hydrogen bromide In toluene for 72h; Heating;
	With hydrogen bromide In cyclohexane for 6h; Heating;
	In hexane; hydrogen bromide	3 10-Bromo-1-decanol EXAMPLE 3 10-Bromo-1-decanol A solution of 1,10-dihydroxydecane (80 g) in 47% hydrobromic acid (650 ml) was stirred at 80° C. whilst being continuously extracted with petroleum ether (boiling range 80°-100°), for 24 hours. The organic extracts were neutralised with solid potassium carbonate, filtered, and the filtrates evaporated to dryness. The resultant dark oil was fractionally distilled (Vigreaux apparatus) to give a colourless oil, boiling point 102°-104° (0.01 mm Hg). Part of this oil (52 g) was purified by preparative HPLC (silica; eluents:diethyl ether/hexane 1:1) to remove a significant 1,10-dibromodecane impurity, finally yielding the title compound as a colourless oil.
	In hexane; hydrogen bromide	3 10-Bromo-1-decanol EXAMPLE 3 10-Bromo-1-decanol A solution of 1,10-dihydroxydecane (80 g) in 47% hydrobromic acid (650 ml) was stirred at 80°C whilst being continuously extracted with petroleum ether (boiling range 80-100°), for 24 hours. The organic extracts were neutralised with solid potassium carbonate, filtered, and the filtrates evaporated to dryness. The resultant dark oil was fractionally distilled (Vigreaux apparatus) to give a colourless oil, boiling point 102-104° (0.01 mm Hg). Part of this oil (52 g) was purified by preparative HPLC (silica; eluents:diethyl ether/hexane 1:1) to remove a significant 1,10-dibromodecane impurity, finally yielding the title compound as a colourless oil.
	With hydrogen bromide In toluene for 16h; Reflux;
73.47 mg	With hydrogen bromide In benzene for 2.5h; Reflux;
	With hydrogen bromide In toluene for 75h; Reflux;
	With hydrogen bromide In toluene at 120℃; for 16h;	4.1.2. General Synthesis Procedure for Bromoalcohols 8a, 8b,and 8c. To a stirred solution of diol 7 (300 mmol, 1.0 equiv)in toluene (600 mL) was added slowly 48% HBr (360 mmol,1.2 equiv) at RT. -e reaction mixture was reLuxed at 120°Cfor 16 h. After cooling to 0°C for 30 min, the organic layerwas separated and washed with saturated NaHCO3 solution.-e resulting aqueous layer was extracted with hexane(120 mL× 3). -e combined organic layer was washed withbrine (300 mL), dried over anhydrous MgSO4, :ltered, andconcentrated in vacuo to obtain the corresponding bromoalcohol8 as a light yellow oil. -e crude bromoalcohol 8was employed in the next step without further puri:cation.Bromoalcohols 8a, 8b, and 8c were synthesized independentlyaccording to the general procedure with 90%, 85%,and 91% yields, respectively. 1H NMR (200 MHz, CDCl3 ppm) for 8a: δ 3 3.63 (t, J 6.5 Hz, 2H), 3.40 (t, J 6.8 Hz, 2H),1.90-1.75 (m, 2H), 1.55-1.40 (m, 3H), 1.40-1.20 (m, 12H);13C NMR (100 MHz, CDCl3, ppm) for 8a: δ 3 62.54, 33.76,32.66, 32.53, 29.33, 29.24, 29.21, 28.58, 27.99, 25.59.
	With hydrogen bromide In water; toluene for 48h; Reflux;

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[60]Location in patent: experimental part Gansca, Lucia; Andreica, Adriana; Ciotlaus, Irina; Maxim, Sanda; Oprean, Ioan [Revue Roumaine de Chimie, 2011, vol. 56, # 7, p. 705 - 709]
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[63]Kranthikumar, Ramagonolla [Organic and Biomolecular Chemistry, 2021, vol. 19, # 45, p. 9833 - 9839]

8
[ 112-47-0 ]
[ 2162-98-3 ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2002,vol. 28,p. 62 - 64
[2]Journal of Organic Chemistry,1953,vol. 18,p. 728,731,733
[3]Journal of the American Chemical Society,1951,vol. 73,p. 2730,2731
[4]Pharmaceutical Chemistry Journal,1972,vol. 6,p. 283 - 286
Khimiko-Farmatsevticheskii Zhurnal,1972,vol. 6,p. 11 - 14
[5]Synthetic Communications,2001,vol. 31,p. 367 - 373

9
[ 112-47-0 ]
[ 16355-92-3 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 8805 - 8810
[2]Journal of the Chemical Society,1952,p. 142,144
[3]Journal of Physical Chemistry,1989,vol. 93,p. 3479 - 3483
[4]Journal of the Chinese Chemical Society,1995,vol. 42,p. 641 - 650
[5]Journal of Physical Chemistry B,1997,vol. 101,p. 1058 - 1062
[6]Journal of Medicinal Chemistry,2000,vol. 43,p. 1413 - 1417
[7]Russian Journal of Bioorganic Chemistry,2002,vol. 28,p. 62 - 64

10
[ 112-47-0 ]
[ 4101-68-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrogen bromide In octane; water at 145℃; for 7h; Dean-Stark;	General procedure General procedure: A one-neck rb flask was charged with diol (1equiv), 48% aq HBr (~3 equiv/OH), octane (~7:1 v/w ratio vs diol), fitted tothe fractionating column/Dean-Stark trap, and heated inan oil bath (145-150 °C) w/rapid magnetic stirring. The aqueous (lower) layer of the initialazeotrope condensate (bp 89-92 °C) was tapped offuntil about half of the theoretical amount of H2O had been collected;the azeotrope temp (still head) then began to rise. The condenser was set to total reflux forseveral h, reopened, and aq material collected for 1h more (head temp 96-100°C). The final volume of aq distillatewas 90-100+% of theory (higher-boiling distillate contained up to 24% HBr). When the (pale tan) octane phase containedboth dibromide and bromoalkanol (6band 6c), washing with cold 85% v/v H2SO4 (10 mL,then 5 mL) removed all color and all bromoalkanol. For all three dibromides (3b, 4b, 6b) the neutralized octane solutionwas stripped of solvent (vigreux column, reduced pressure), and the essentiallypure residue (1H NMR) was kugelrohr distilled. A trace of 4-methyltetrahydropyran was foundin 4b before distillation.
86%	With hydrogen bromide In water at 100℃; for 48h;
80%	With hydrogen bromide In water at 100℃; for 48h;

	With sulfuric acid; hydrogen bromide
	With sulfuric acid; sodium bromide
	With hydrogen bromide at 60℃;
	With hydrogen bromide at 100℃;
	With hydrogen bromide
	With hydrogen bromide at 95℃; anschliessendes Erhitzen im HBr-Strom auf 135grad;
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 0.25 h / Ambient temperature 2: LiBr / tetrahydrofuran; hexamethylphosphoric acid triamide / 4 h / Heating

Reference： [1]Mekala, Shekar; Hahn, Roger C. [Tetrahedron Letters, 2015, vol. 56, # 4, p. 630 - 632]
[2]Ikenberry, Myles; Pena, Leidy; Wei, Daming; Wang, Hongwang; Bossmann, Stefan H.; Wilke, Trenton; Wang, Donghai; Komreddy, Venugopal R.; Rillema, D. Paul; Hohn, Keith L. [Green Chemistry, 2014, vol. 16, # 2, p. 836 - 843]
[3]Listunov, Dymytrii; Fabing, Isabelle; Saffon-Merceron, Nathalie; Gaspard, Hafida; Volovenko, Yulian; Maraval, Valérie; Chauvin, Remi; Génisson, Yves [Journal of Organic Chemistry, 2015, vol. 80, # 11, p. 5386 - 5394]
[4]Stone [Journal of the American Chemical Society, 1936, vol. 58, p. 488]
[5]Taylor [Journal of the Chemical Society, 1958, p. 2068]
[6]Franke; Hankam [Monatshefte fur Chemie, 1910, vol. 31, p. 181]
[7]Jegorow [Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1910, vol. 42, p. 1658][Chemisches Zentralblatt, 1911, vol. 82, # I, p. 1500]
[8]Chuit [Helvetica Chimica Acta, 1926, vol. 9, p. 265]
[9]Carothers et al. [Journal of the American Chemical Society, 1930, vol. 52, p. 5281] McEwen [Organic Syntheses, 1940, vol. 20, p. 24]
[10]Camps, Francisco; Gasol, Vicens; Guerrero, Angel [Synthesis, 1987, # 5, p. 511 - 512]

11
[ 112-47-0 ]
[ 53463-68-6 ]
[ 4101-68-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 9% 2: 88%	With hydrogen bromide In cyclohexane for 6h; Heating;
87%	With hydrogen bromide In toluene for 48h; Heating;
87%	With hydrogen bromide In water; toluene Reflux;

73%	With hydrogen bromide
1: 64% 2: 10%	With tetrabutylammomium bromide; hydrogen bromide In water at 105℃; for 2h; chemoselective reaction;
45%	With tetrabutylammomium bromide; hydrogen bromide In water at 100℃; for 0.0833333h; Microwave irradiation;
	With hydrogen bromide at 130℃;
	With hydrogen bromide In para-xylene; water at 130 - 135℃; for 6.5h; Dean-Stark;	General procedure General procedure: A one-neck rb flask was charged with diol (1equiv), 48% aq HBr (~3 equiv/OH), octane (~7:1 v/w ratio vs diol), fitted tothe fractionating column/Dean-Stark trap, and heated inan oil bath (145-150 °C) w/rapid magnetic stirring. The aqueous (lower) layer of the initialazeotrope condensate (bp 89-92 °C) was tapped offuntil about half of the theoretical amount of H2O had been collected;the azeotrope temp (still head) then began to rise. The condenser was set to total reflux forseveral h, reopened, and aq material collected for 1h more (head temp 96-100°C). The final volume of aq distillatewas 90-100+% of theory (higher-boiling distillate contained up to 24% HBr). When the (pale tan) octane phase containedboth dibromide and bromoalkanol (6band 6c), washing with cold 85% v/v H2SO4 (10 mL,then 5 mL) removed all color and all bromoalkanol. For all three dibromides (3b, 4b, 6b) the neutralized octane solutionwas stripped of solvent (vigreux column, reduced pressure), and the essentiallypure residue (1H NMR) was kugelrohr distilled. A trace of 4-methyltetrahydropyran was foundin 4b before distillation.

Reference： [1]Girlanda-Junges, Celine; Keyling-Bilger, Florence; Schmitt, Gaby; Luu, Bang [Tetrahedron, 1998, vol. 54, # 27, p. 7735 - 7748]
[2]Chong, J. Michael; Heuft, Matthew A.; Rabbat, Phil [Journal of Organic Chemistry, 2000, vol. 65, # 18, p. 5837 - 5838]
[3]Location in patent: body text Banaszak, Estelle; Xu, Li-Wen; Bardeau, Jean-François; Castanet, Anne-Sophie; Mortier, Jacques [Tetrahedron, 2009, vol. 65, # 20, p. 3961 - 3966]
[4]Thijs; Zwanenburg [Tetrahedron, 2004, vol. 60, # 24, p. 5237 - 5252]
[5]Location in patent: experimental part Spaccini, Raffaele; Tsoukala, Anna; Liguori, Lucia; Punta, Carlo; Borsvik, Hans-Rene [Organic Process Research and Development, 2010, vol. 14, # 5, p. 1215 - 1220]
[6]Location in patent: experimental part Tsoukala, Anna; Bjorsvik, Hans-Rene [Organic process research and development, 2011, vol. 15, # 3, p. 673 - 680]
[7]Chuit [Helvetica Chimica Acta, 1926, vol. 9, p. 226]
[8]Mekala, Shekar; Hahn, Roger C. [Tetrahedron Letters, 2015, vol. 56, # 4, p. 630 - 632]

12
[ 110-40-7 ]
[ 112-47-0 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 1173 - 1174
[2]Russian Journal of Bioorganic Chemistry,2002,vol. 28,p. 62 - 64
[3]Journal of the American Chemical Society,1947,vol. 69,p. 2352
[4]Journal of the American Chemical Society,1949,vol. 71,p. 3246
[5]Journal of the Chemical Society,1931,p. 1699
[6]Journal of the American Chemical Society,1933,vol. 55,p. 1293
[7]Journal of the American Chemical Society,1933,vol. 55,p. 1293
[8]Journal of the American Chemical Society,1947,vol. 69,p. 2352
[9]Journal of the American Chemical Society,1932,vol. 54,p. 1146
[10],1934,vol. 14,p. 20
[11]Bulletin of the Chemical Society of Japan,1974,vol. 47,p. 2739 - 2744
[12]Patent: US2228268,1938,
[13]Patent: US2091800,1931,
[14]Patent: DE655198,1932,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 24,p. 266
[15]Patent: DE655198,1932,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 24,p. 266

13
[ 112-47-0 ]
[ 141-75-3 ]
[ 80054-63-3 ]

Yield	Reaction Conditions	Operation in experiment
41%	With dmap; triethylamine In dichloromethane at 0 - 20℃;	2-Hydroxyethyl Dodecanoate (13a) General procedure: Ethanediol (1.1 mL, 20.00 mmol), Et3N (5.10 g, 50.0 mmol) and DMAP (122 mg, 1.0 mmol) were dissolved in 200 mL anhydrous CH2Cl2. The C11H23COCl (2.18 g, 10.00 mmol) was added dropwise at 0 °C. The mixture was warmed up to room temperature and kept stirring overnight then washed with 1 N HCl solution, water, saturated aqueous solution of NaHCO3and brine, successively. The organic phase was dried overNa2SO4, filtered, and then concentrated. The crude mixture was purified by column chromatography (petroleum ether-EtOAc 30 : 1) on silica gel to afford 13a as a colorless oil (1.51 g, 62%).
	With pyridine

14
[ 112-47-0 ]
[ 814-68-6 ]
[ 13048-34-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In tetrahydrofuran

Reference： [1]Skinner,W.A. et al. [Journal of Medicinal Chemistry, 1966, vol. 9, p. 605 - 607]

15
[ 110-87-2 ]
[ 112-47-0 ]
[ 43047-93-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 1-butyl-3-methylimidazolium hydrogen sulfate In hexane microwave irradiation;
97%	With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 24h;
89%	With tetrachlorosilane In dichloromethane at 20℃; for 0.666667h;

89%	With sodium hydrogen sulfate In hexane; water; dimethyl sulfoxide at 40℃; for 16h;	General procedure for the synthesis of monotetrahydropyranyl acetals 2a-d General procedure: A mixture of 1,n-diols 1a-d (1.0 mmol), DHP-hexane 3% (v/v) (1.96 mmol) and aqueous 5 M NaHSO4 (01 mL) was prepared. To 1,10-decanediol 1c and 1,12-dodecanediol 1d, 0.2 mL of DMSO were also added to the mixture at the beginning of the reaction. This mixture was stirred at 40 °C for 16 h and then extracted with hexane (3 × 20 mL). The combined organic phases were dried (Na2SO4), filtered and then evaporated under reduced pressure. The residue obtained was chromatographed using silica gel using hexane/EtOAc (8:2) to yield pure Compounds 2a-d.
66%	With pyridinium p-toluenesulfonate In chloroform
53%	With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 2h;
53%	With toluene-4-sulfonic acid In tetrahydrofuran; dichloromethane at 0 - 20℃; for 12h;
49%	With pyridinium p-toluenesulfonate In tetrahydrofuran; chloroform-d1 at 20℃; Inert atmosphere;
48%	With toluene-4-sulfonic acid In tetrahydrofuran; dichloromethane; water at 20 - 25℃; for 9h; Inert atmosphere;	2.7 Synthesis of 10-(tetrahydro-2H-pyran-2-yloxy)decan-1-ol 41 To a stirred solution of 1,10-decanediol (10.3 g, 59.3 mmol) in anhydrous mixture of THF:DCM (2:1, 300 mL) at 0°C under an argon atmosphere was added a catalytic amount of p-toluenesulfonic acid monohydrate (0.89 g, 4.74 mmol, 8 mol%), followed by dihydropyran (5.4 mL, 58.2 mmol). After being stirred for 1h at the same conditions and for additional 8h at ambient temperature (as monitored by TLC analysis cyclohexane/ EtOAc 3:2; Rf (adduct)= 0.37; Rf (product)=0.68; visualized with Seebach reagent), the reaction mixture was diluted with diethylether (200 mL) and carefully quenched with saturated aqueous NaHCO3 solution (150 mL). The resultant mixture was extracted with diethylether (3x100 mL), and the combined organic layers were washed with brine (150 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The resulting crude mixture was purified by flash column chromatography over silica gel using cyclohexane and ethylacetate as eluents (from 15-20% ethylacetate in cyclohexane) provided compound 41 as colorless oil. Yield: 7.5 g (48%). Rf: 0.68 (cyclohexane/EtOAc 3:2, Seebach reagent). 1H NMR (CDCl3, 500 MHz, ppm) δ 4.56 (dd, J = 4.3, 2.8 Hz, 1H), 3.85 (ddd, J = 11.2, 7.6, 3.2 Hz, 1H), 3.71 (dt, J = 9.6, 6.9 Hz, 1H), 3.60 (t, J = 6.7 Hz., 2H), 3.51 - 3.45 (m, 1H), 3.36 (dt, J = 9.6, 6.7 H, 1Hz), 1.86 - 1.77 (m, 1H), 1.73 - 1.66 (m, 1H), 1.60 - 1.47 (m, 8H), 1.37 - 1.25 (m, 12H). 13C NMR (CDCl3, 126 MHz, ppm) δ 98.91, 67.77, 63.02, 62.40, 32.86, 30.84, 29.80, 29.62, 29.58, 29.53, 29.49, 26.29, 25.82, 25.57, 19.74. HRMS (ESI+) m/z calcd for C15H30O3Na [M+Na]+ 281.2093; observed 281.2087.
41%	With toluene-4-sulfonic acid In tetrahydrofuran at -5℃; for 48h;
	With toluene-4-sulfonic acid In dichloromethane
	With toluene-4-sulfonic acid In dichloromethane at 20℃; for 3h; regioselective reaction;
	With sodium hydrogen sulfate In hexane; dimethyl sulfoxide at 40℃; for 16h;

Reference： [1]Singh, Jasvinder; Gupta, Neeraj; Kad, Goverdhan L.; Kaur, Jasamrit [Synthetic Communications, 2006, vol. 36, # 19, p. 2893 - 2900]
[2]Huang, Xuebin; Liu, Yunqi; Wang, Shuai; Zhou, Shuqin; Zhu, Daoben [Chemistry - A European Journal, 2002, vol. 8, # 18, p. 4179 - 4184]
[3]Ravindranath; Ramesh; Das [Synlett, 2001, # 11, p. 1777 - 1778]
[4]Gonalves, Alessandra Mirtes Marques Neves; De Lima, Aline Brito; Da Silva Barbosa, Maria Cristina; De Camargos, Luiz Fernando; De Oliveira, Jlia Teixeira; De Souza Barbosa, Camila; Villar, Jos Augusto Ferreira Perez; Costa, Andr Carvalho; Da Silva, Isabella Viana Gomes; Silva, Luciana Maria; De Pilla Varotti, Fernando; Dos Santos, Fabio Vieira; Viana, Gustavo Henrique Ribeiro [Marine Drugs, 2014, vol. 12, # 8, p. 4361 - 4378]
[5]Hakogi, Toshikazu; Shigenari, Toshihiko; Katsumura, Shigeo; Sano, Takamitsu; Kohno, Takayuki; Igarashi, Yasuyuki [Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 4, p. 661 - 664]
[6]Centrone, Charla A.; Lowary, Todd L. [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 21, p. 5495 - 5503]
[7]Steiner, Regula; Saied, Essa M.; Othman, Alaa; Arenz, Christoph; Maccarone, Alan T.; Poad, Berwyck L. J.; Blanksby, Stephen J.; Von Eckardstein, Arnold; Hornemann, Thorsten [Journal of Lipid Research, 2016, vol. 57, # 7, p. 1194 - 1203]
[8]Hwang, Yoon Soo; Yim, Junhyeong; Song, Heebum; Park, Seung Bum [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 5, p. 720 - 725]
[9]Saied, Essa M.; Le, Thuy Linh-Stella; Hornemann; Arenz, Christoph [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 4047 - 4057]
[10]Hirst, David; Diele, Siegmar; Laschat, Sabine; Nimtz, Manfred [Helvetica Chimica Acta, 2001, vol. 84, # 5, p. 1190 - 1196]
[11]Furukawa, Yoshiaki; Yamagiwa, Yoshiro; Kamikawa, Tadao [Journal of the Chemical Society. Chemical communications, 1986, # 16, p. 1234 - 1235]
[12]Location in patent: body text Shingala, Shailesh D.; Venkateswar Reddy; Sateesh Chandra Kumar; Ashok Yadav; Suresh Babu [Journal of Asian Natural Products Research, 2011, vol. 13, # 2, p. 128 - 135]
[13]Evangelista, Fernanda Cristina Gontijo; de Freitas Lopes, Aline; Andrade, Silmara Nunes; de Souza Barbosa, Camila; da Silva, Julia Dias; Neves, Alessandra Mirtes Marques; de Mello Gomide Loures, Cristina; Brito, Larissa Froede; de Sousa, Lirlândia Pires; Borges, Karina Braga Gomes; Viana, Gustavo Henrique Ribeiro; de Pilla Varotti, Fernando; de Paula Sabino, Adriano [Medicinal Chemistry Research, 2019, vol. 28, # 9, p. 1567 - 1578] Zhou, Shiyang; Huang, Gangliang; Chen, Guangying [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 41]

16
[ 112-47-0 ]
[ 1732-09-8 ]
1,12-Dioxa-cyclohexacosane-13,26-dione [ No CAS ]
C₄₈H₈₈O₈ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1999 - 2001

17
[ 112-47-0 ]
[ 821-38-5 ]
1,12-Dioxa-cyclohexacosane-13,26-dione [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1999 - 2001

18
[ 112-47-0 ]
[ 821-38-5 ]
1,12-Dioxa-cyclohexacosane-13,26-dione [ No CAS ]
C₄₈H₈₈O₈ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1999 - 2001

19
[ 112-47-0 ]
[ 13726-67-5 ]
[ 124212-51-7 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 741 - 748

20
[ 112-47-0 ]
[ 13019-22-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 1-hexadecylcarboxylic acid at 340℃; for 5h; Molecular sieve;	1-1 Synthesis of 9-decenol (Cyclic reaction) 18 g of the vacuum distillation bottoms liquid obtained in the step 2) of Example 1 was mixed with fresh raw material - 1,10-decanediol (which may be mixed in any ratio), and the resulting mixture was used in place of that used in the step 1) 1, 10-decanediol was continuously fed and then the reaction was continued according to the process conditions of step 1) of Example 1; namely, the discharge rate was adjusted to 30 g / h, and the feed rate was adjusted to be consistent with the discharge rate .The reaction was continued for 6 hours, feeding 190 g and discharging about 180 g.And then subjected to atmospheric distillation and vacuum distillation as in Example 1, step 2) to obtain 9-decenol, yield 88%, and purity 99.3%.Based on the above data, we know that the above-mentioned cyclic reaction does not affect the final yield and product purity.
80%	With 1-hexadecylcarboxylic acid; stearic acid at 330 - 350℃; for 150h;
		1 EXAMPLE 1 The oil amounting to 1372 g was then fractionated using a 30-plate Heli-pak (a product from Podbielniak, Inc.) packed column to obtain 885 g of the desired product, 9-decene-1-ol, as the distillate at 74° C./l mm Hg; 270 g of the unreacted 1,10 -decanediol; 16 g of the by-produced decadienes and 201 g of the by-produced decene-1-ols. The identification of the desired product, 9-decene-1-ol, was established by the following analytical results. MS (m/e): 156 (M+); IR (cm-1, neat): 3070, 1643, 995 and 910; NMR (δ, ppm, 20% in CCl4 solution): 4.74-6.04 STR1 3.45 (2H, t, J=6 cps, --CH2 --CH2 --OH), 2.02 (2H, t, d, J=6 cps, STR2 1.28 (12H, b. s., --(CH2)n --) and 4.23 (1H, s, --CH2 OH).

	Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; hydrogen bromide / water / 0.08 h / 100 °C / Microwave irradiation 2: potassium <i>tert</i>-butylate / tetrahydrofuran; toluene / 0.5 h / 0 °C
	With scandium(III) oxide In ethanol at 350℃; for 5h; Inert atmosphere;

Reference： [1]Current Patent Assignee: HANGZHOU KAIMING PANGDE BIOTECHNOLOGY - CN105330516, 2016, A Location in patent: Paragraph 0039; 0040
[2]Yamanaka, Tohr; Imai, Takashi [Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 5, p. 1585 - 1586]
[3]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - US4288642, 1981, A
[4]Tsoukala, Anna; Bjorsvik, Hans-Rene [Organic process research and development, 2011, vol. 15, # 3, p. 673 - 680]
[5]Location in patent: experimental part Abe, Katsutoshi; Ohishi, Yusuke; Okada, Takuto; Yamada, Yasuhiro; Sato, Satoshi [Catalysis Today, 2011, vol. 164, # 1, p. 419 - 424]

21
[ 106-79-6 ]
[ 112-47-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium tetrahydridoborate; ethanol; cerium(III) trichloride heptahydrate at 20℃; for 24h; chemospecific reaction;
70%	With <i>tert</i>-butyl alcohol In tetrahydrofuran electrolysis (Mg electrodes, LiClO₄);
	With zinc(II) tetrahydroborate In 1,2-dimethoxyethane for 24h; sonication; or with N,N-dimethylaniline, 14 h;

	With hydrogen In methanol at 240℃; Flow reactor;	1 (1), mixing the methanol and the sebacic acid dimethyl ester at a mass ratio of 2: 3; (2) mixing the hydrogen with the raw material in the step (1) at a certain ratio of hydrogen to the fixed bed reactor Premixer (3), the mixed raw materials of step (2) were continuously fed into a fixed bed equipped with 10 ml of a 2-gauge (Cu / Zn0 / Al203 catalyst (Cu 50% wt, Zn040% wt, Al203 10% wt) The reactor is subjected to a hydrogenation reaction under certain conditions. (The specific conditions shown in Table 1); (4), the product into the separator, separation of 1,10-decanediol.
89 %Spectr.	With samarium diiodide; triethylamine In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 2h; Inert atmosphere; regioselective reaction;

Reference： [1]Location in patent: experimental part Xu, Yinan; Wei, Yunyang [Synthetic Communications, 2010, vol. 40, # 22, p. 3423 - 3429]
[2]Shono, Tatsuya; Masuda, Haruhisa; Murase, Hiroaki; Shimomura, Masatoshi; Kashimura, Shigenori [Journal of Organic Chemistry, 1992, vol. 57, # 4, p. 1061 - 1063]
[3]Ranu, Brindaban C.; Basu, Manas K. [Tetrahedron Letters, 1991, vol. 32, # 27, p. 3243 - 3246]
[4]Current Patent Assignee: CHINA PETROCHEMICAL CORPORATION - CN105503527, 2016, A Location in patent: Paragraph 0017-0018
[5]An, Jie; Dong, Yanhong; Li, Hengzhao; Liu, Shangzhong; Ning, Lei; Peng, Mengqi; Qin, Zixuan; Wang, Lijun [Synlett, 2022, vol. 33, # 8, p. 771 - 776]

22
[ 112-47-0 ]
[ 33252-29-8 ]
[ 104727-45-9 ]
[ 104727-44-8 ]

Reference： [1]Tetrahedron,1985,vol. 41,p. 4941 - 4948

23
[ 112-47-0 ]
[ 33252-29-8 ]
[ 104727-44-8 ]

Reference： [1]Tetrahedron,1985,vol. 41,p. 4941 - 4948

24
[ 112-47-0 ]
[ 33252-29-8 ]
[ 104727-53-9 ]

Reference： [1]Tetrahedron,1985,vol. 41,p. 4941 - 4948

25
[ 112-47-0 ]
[ 124-63-0 ]
[ 32366-73-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine In dichloromethane at 0℃; for 3h; Inert atmosphere;	6 4.6 5-(Benzyloxy)pentyl methanesulfonate (7a) [47] General procedure: Freshly distilled methanesulphonyl chloride (2.3 mL, 30.9 mmol) was added drop wise to a stirred solution of 5-(benzyloxy)pentane-1-ol (4 g, 20.6 mmol) and Et3N (4.3 mL, 31 mmol) in dry dichloromethane (45 mL) at 0 °C. After 3 h, the reaction mixture was diluted with water, and extracted with dichloromethane. The organic extract was concentrated under vacuum to give mesylate 7a (5.3 g, 95%). IR (film): υυ 3427, 3034, 2943, 2860, 2519, 2315, 1959, 1732, 1460, 1352, 1172, 1096, 952, 832, 741, 695, 612, 521 cm-1. 1H NMR (200 MHz, CDCl3): δ 1.50-1.85 (m, 6H, 3 × CH2), 2.99 (s, 3H, OSO2CH3), 3.48 (t, 2H, 3JHH = 6.0 Hz, CH2OCH2Ph), 4.22 (t, 2H, 3JHH = 6.4 Hz, SO2CH2), 4.50 (s, 2H, PhCH2), 7.27-7.35 (m, 5H, Ph). 13C NMR (50 MHz, CDCl3): δ 22.0, 28.6, 28.8, 36.9, 69.6, 69.9, 72.6, 127.3, 127.4 (2C), 128.1 (2C), 138.3.
93%	With triethylamine In tetrahydrofuran; dichloromethane for 15h; Ambient temperature;
65%	With pyridine at 0℃;

31.6%	With triethylamine In dichloromethane at 0 - 20℃; for 19h; Inert atmosphere;	1-1 Synthesis Example 1-1: Preparation of Compound 1-1 1,10-decanediol (10.0 g, 57.37 mmol, 1 eq) was dissolved in 25 mL of anhydrous MC under an argon stream, triethylamine was added thereto, (40.0 mL, 17.21 mmol) was added and the temperature was lowered to 0 & lt; 0 & gt; C. Methanesulfonylchloride (4.7 mL, 4.07 mmol) was slowly added to the reaction mixture, stirred at 0 ° C. for 1 hour, then heated to room temperature and further stirred for 18 hours. After completion of the reaction, the reaction mixture was washed with ice water, and purified water and dichloromethane were added. After stirring briefly, the organic layer and the water layer were separated and the organic layer was collected and washed with a 10% sodium chloride aqueous solution. The residue was purified by silica gel column chromatography (eluent: 80% EtOAc-Hexanes) to give Compound 1-1 as a yellow solid (g, 31.6%).
31.6%	With triethylamine at 0 - 20℃; for 19h; Inert atmosphere;	1-1 Synthesis Example 1-1: Preparation of Compound 1-1 Under an argon stream 1,10-decanediol (10.0 g, 7.37 mmol, 1 eq) was dissolved in anhydrous MC (25 mL), and then triethylamine (40.0 mL, 17.21 mmol) was added thereto and the temperature was lowered to 0 ° C.Methanesulfonylchloride (4.7 mL, 4.07 mmol) was slowly added to the reaction mixture, stirred at 0 ° C. for 1 hour, then heated to room temperature and further stirred for 18 hours. After completion of the reaction, the reaction mixture was washed with ice water, and purified water and dichloromethane were added. After stirring briefly, the organic layer and the water layer were separated and the organic layer was collected and washed with a 10% sodium chloride aqueous solution.After the water remaining in the organic layer was removed with magnesium sulfate, the solution was concentrated and purified by silica gel column chromatography(Eluent: 80% EtOAc-Hexanes) to give Compound 1-1 as a yellow solid (g, 31.6%).
	With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	4.2. General procedure for the formation of α,ω-bis(methanesulfonyloxy)alkanes General procedure: Under an atmosphere of nitrogen, the α,ω-alkanediol (8.5 mmol, 1equiv) was dissolved in warm tetrahydrofuran (20 mL) and the solutionwas then cooled to 0 °C. To this solution was added triethylamine (2.5equiv) and then methanesulfonyl chloride (2.2 equiv). The mixture wasstirred at room temperature overnight, concentrated, and then driedunder high vacuum. Water was added, and the resulting solid wascollected by filtration and washed with water (250 mL). The solidmaterial was dried under high vacuum to give the product.

Reference： [1]Paramanik, Minakshmi; Singh, Rekha; Mukhopadhyay, Sulekha; Ghosh, Sunil K. [Journal of Fluorine Chemistry, 2015, vol. 178, p. 47 - 55]
[2]Hosseini, Mir Wais; Lehn, Jean-Marie [Helvetica Chimica Acta, 1986, vol. 69, p. 587 - 603]
[3]Cheng, P.; Blumstein, A.; Subramanyam, S. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 269, p. 1 - 38]
[4]Current Patent Assignee: BIO ACTS CO.,LTD. - KR101946488, 2019, B1 Location in patent: Paragraph 0061-0063
[5]Current Patent Assignee: BIO ACTS CO.,LTD. - KR2019/30527, 2019, A Location in patent: Paragraph 0077-0079
[6]Brockhausen, Inka; Kocev, Alexander; Kong, Xianqi; Melamed, Jacob; Szarek, Walter A.; Vlahakis, Jason Z.; Wang, Shuo; Xu, Yaozu [Bioorganic and medicinal chemistry, 2020]

26
[ 112-47-0 ]
[ 98-59-9 ]
[ 36247-33-3 ]

Yield	Reaction Conditions	Operation in experiment
90.9%	With pyridine In dichloromethane at 5 - 15℃; for 0.333333h;
86%	With pyridine at 0℃; for 0.5h;
85%	With pyridine at 0℃; for 2.5h;

67%	With pyridine at 0℃;
40%	With pyridine for 24h; Ambient temperature;

Reference： [1]Hogan, John C.; Gandour, Richard D. [Journal of Organic Chemistry, 1992, vol. 57, # 1, p. 55 - 61]
[2]Luscombe, Christine K.; Proemmel, Steffen; Huck, Wilhelm T. S.; Holmes, Andrew B.; Fukushima, Hitoshi [Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5505 - 5513]
[3]Walczak, Ryan M.; Cowart Jr., John S.; Reynolds, John R. [Journal of Materials Chemistry, 2007, vol. 17, # 3, p. 254 - 260]
[4]Cheng, P.; Blumstein, A.; Subramanyam, S. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 269, p. 1 - 38]
[5]Pang, Yuan-Ping; Hong, Feng; Quiram, Polly; Jelacic, Tanya; Brimijoin, Stephen [Journal of the Chemical Society. Perkin transactions I, 1997, # 2, p. 171 - 176]

27
[ 112-47-0 ]
[ 98-59-9 ]
[ 56401-31-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine In dichloromethane; N,N-dimethyl-formamide at 25℃; for 16h;	Synthesis of GalNAc-9 To a solution of decane-l,10-diol (125 g, 717.23 mmol, 5.00 equiv.) in (0227) dichloromethane/N,N-dimethylformamide (250 mL/250 mL) was added triethylamine (21.8 g, 215.44 mmol, 1.50 equiv.). This was followed by the addition of 4-toluolsulfonyl chloride (27.3 g, 143.19 mmol, 1.00 equiv.) at 25°C. The resulting solution was stirred for 16 h at 25°C. The resulting mixture was concentrated under vacuum and diluted with 500 mL of dichloromethane. The solids were filtered out. The resulting solution washed with 3x500 mL of water and 3x500 mL of saturated sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was applied onto a silica gel column. This resulted in 41 g (87%) of G9-1 as colorless oil.
78%	With triethylamine In dichloromethane at 20℃;
46%	With triethylamine Ambient temperature;

46%	With triethylamine In dichloromethane	R.1 1,10-Decanediol monotosylate REFERENCE EXAMPLE 1 1,10-Decanediol monotosylate 174.0 g (1.0 mole) of 1,10-decanediol was added to 1,000 ml of dry triethylamine and 95.0 g (0.5 mole) of p-toluenesulfonyl chloride was added thereto over a period of 6 hours with stirring under ice cooling. The reaction mixture was stirred at room temperature for 16 hours and concentrated under reduced pressure, and 1.5 liters of dichloromethane was added to the residue. The resulting mixture was washed with 100 ml each of water, 2N-HCl, water and an aqueous solution saturated with NaHCO3, respectively in order. The mixture after filtration was concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel (Merck, Art 7734, 1.7 kg; eluent: chloroform-methanol=99:1-98:2) to give 75.6 g of the above-mentioned compound. (yield: 46.0%) Thin-layer chromatography (developing solvent: chloroform-methanol=9:1) Rf=0.70. NMR (90 MHz, CDCl3)δ: 1.25 (16H), 1.42-1.63 (2H), 2.45 (3H), 3.62 (2H), 4.01 (2H), 7.31 (2H), 7.78 (2H)
43%	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 96h; Inert atmosphere;
38%	With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	2.1 Step 1. Preparation of 10-hydroxydecyl 4-methylbenzenesulfonate (2-2) To a mixture of 2-1 (1050 mg, 6.0 mmol, 1.0 eq), DMAP (366 mg, 3.0 mmol, 0.5 eq) and TEA (2430 mg, 24.0 mmol, 4.0 eq) in DCM (30 mL) was added TsCl (1370 mg, 7.2 mmol, 1.2 eq) at 0 °C under N2 atmosphere. Then the mixture was stirred at room temperature overnight. The mixture was then purified by flash column chromatography (60 g, 0-20% EA in PE, 254 nm, 280 nm) to obtain 2-2 as a yellow solid (740 mg, 38% yield).
	With triethylamine

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2019/53661, 2019, A2 Location in patent: Paragraph 0118
[2]Yi, Long; Shi, Jie; Gao, Shuang; Li, Shibo; Niu, Congwei; Xi, Zhen [Tetrahedron Letters, 2009, vol. 50, # 7, p. 759 - 762]
[3]Ukawa; Imamiya; Yamamoto; Mizuno; Tasaka; Terashita; Okutani; Nomura; Kasukabe; Hozumi; Kudo; Inoue [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 5, p. 1249 - 1255]
[4]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US4778912, 1988, A
[5]Utsumi, Tatsuki; Noda, Kenta; Kawauchi, Daichi; Ueda, Hirofumi; Tokuyama, Hidetoshi [Advanced Synthesis and Catalysis, 2020, vol. 362, # 17, p. 3583 - 3588]
[6]Current Patent Assignee: REYOUNG; REYOUNG DRUG DISCOVERY - WO2021/202669, 2021, A2 Location in patent: Paragraph 0175
[7]Location in patent: scheme or table Lukac, Milos; Mrva, Martin; Fischer-Fodor, Eva; Lacko, Ivan; Bukovsky, Marian; Miklasova, Natalia; Ondriska, Frantisek; Devinsky, Ferdinand [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 22, p. 6346 - 6349]

28
[ 818-88-2 ]
[ 112-47-0 ]
[ 2640-94-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 91% 2: 6%	With water In 1,2-dimethoxyethane at 160℃; for 16h;

Reference： [1]He, De-Hua; Wakasa, Noriko; Fuchikami, Takamasa [Tetrahedron Letters, 1995, vol. 36, # 7, p. 1059 - 1062]

29
[ 112-47-0 ]
[ 51309-10-5 ]
[ 2162-98-3 ]

Reference： [1]Chemistry of Natural Compounds,1994,vol. 30,p. 121 - 123
Khimiya Prirodnykh Soedinenii,1994,p. 130 - 132

30
[ 112-47-0 ]
[ 18162-48-6 ]
[ 90934-00-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydride In tetrahydrofuran at 20℃;
64.5%	With 1H-imidazole In dichloromethane at 20℃; Cooling with ice;
58%	With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;

46%	With dmap; triethylamine In dichloromethane at 0℃; for 1h; Inert atmosphere;
42%	With sodium hydride
27%	Stage #1: 1,10-Decanediol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 2h; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil at 20℃;
	With sodium hydride 1.) THF, reflux, 16 h, 2.) THF, 25 deg C, 4 h; Multistep reaction;
	With 1H-imidazole
	In dichloromethane for 24h;
8.44 g	With 1H-imidazole In N,N-dimethyl-formamide for 15h;	1-1 [Experiment 1-1: Synthesis of Alcohol (5)] [Experiment 1-1: Synthesis of Alcohol (5)]5 g of 1,10-decanediol (28.69 mmol) was dissolved in 30 ml of DMF.To this solution, 4.32 g of TBSCl (28.69 mmol) andAnd 1.95 g of imidazole (28.69 mmol) were added,The solution was stirred for 15 h.Saturated sodium hydrogen carbonate aqueous solution was added to the obtained reaction solution,The reaction was stopped.The reaction solution was extracted with a mixed solvent of hexane: ethyl acetate = 1: 1.The organic layer was dried over sodium sulfate,Concentration gave 12.56 g of crude product.The crude product was purified by column chromatography (hexane: ethyl acetate = 5: 1)8.44 g of alcohol (5) (29.25 mmol) was obtained as a colorless oil.
	With 1H-imidazole In dichloromethane at 20℃;

Reference： [1]Liu, Lihua; Bao, Xifei; Xiao, Hua; Li, Junlan; Ye, Feifan; Wang, Chaoqin; Cai, Qinhua; Fan, Shilu [Journal of Organic Chemistry, 2019, vol. 84, # 1, p. 423 - 434]
[2]Huang, Zheng; Zhang, Yi-Mei; Cheng, Qian; Zhang, Ji; Liu, Yan-Hong; Wang, Bing; Yu, Xiao-Qi [Journal of Materials Chemistry B, 2016, vol. 4, # 33, p. 5575 - 5584]
[3]Tully, Sarah E.; Cravatt, Benjamin F. [Journal of the American Chemical Society, 2010, vol. 132, p. 3264 - 3265]
[4]Sawama, Yoshinari; Masuda, Masahiro; Asai, Shota; Goto, Ryota; Nagata, Saori; Nishimura, Shumma; Monguchi, Yasunari; Sajiki, Hironao [Organic Letters, 2015, vol. 17, # 3, p. 434 - 437]
[5]Shin, Youseung; Choy, Nakyen; Balachandran, Raghavan; Madiraju, Charitha; Day, Billy W.; Curran, Dennis P. [Organic Letters, 2002, vol. 4, # 25, p. 4443 - 4446]
[6]Brehm, Elisabeth; Breinbauer, Rolf [Organic and Biomolecular Chemistry, 2013, vol. 11, # 29, p. 4750 - 4756]
[7]Sonnet, Philip E.; Osman, Stanley F.; Gerard, Herve C.; Dudley, Robert L. [Chemistry and Physics of Lipids, 1994, vol. 69, # 2, p. 121 - 128]
[8]Nagano; Tada; Isobe; Yajima [Synlett, 2000, # 8, p. 1193 - 1195]
[9]Location in patent: scheme or table Braunshier, Christian; Hametner, Christian; Fröhlich, Johannes; Schnöller, Johannes; Hutter, Herbert [Tetrahedron Letters, 2008, vol. 49, # 50, p. 7103 - 7105]
[10]Current Patent Assignee: ASAHI GROUP HOLDINGS LTD. - JP2017/100988, 2017, A Location in patent: Paragraph 0110
[11]Gundoju, Narayana Rao; Bokam, Ramesh; Yalavarthi, Nageswara Rao; Buddana, Sudheer Kumar; Prakasham; Ponnapalli, Mangala Gowri [Journal of Asian Natural Products Research, 2018, p. 1 - 8]

31
[ 112-47-0 ]
[ 3634-83-1 ]
5,16-Dioxa-3,18-diaza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,20⁽²⁴⁾,21-triene-4,17-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%	With triethylamine In tetrahydrofuran; toluene for 14h; Heating;

Reference： [1]Irie; Yamamoto; Kishikawa; Kohmoto; Yamada [Synthesis, 1995, # 9, p. 1179 - 1182]

32
1,3-Dioxa-cyclotridecane-4,13-dione [ No CAS ]
[ 111-20-6 ]
[ 112-47-0 ]
[ 1679-53-4 ]

Reference： [1]Synthetic Communications,1997,vol. 27,p. 1697 - 1702

33
[ 112-47-0 ]
[ 100-39-0 ]
[ 95331-19-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With silver(l) oxide In dichloromethane Reflux;	10.a (a) Synthesis of 10-(benzyloxy)decan-1-ol To a stirred suspension of decane-1,10-diol (3 g, 17.21 mmol), benzyl bromide (2.25 ml, 18.94 mmol) and Ag2O (5.98 g, 25.82 mmol) in dry DCM (50 ml) were added, the reaction mixture was refluxed overnight, then the Ag2O was filtered off. The crude product was purified by silica gel column (10% EtOAc in Hexane) to afford 10-(benzyloxy)decan-1-ol as a gummy colorless liquid (2.96 g, 65%). Rf=0.55 (20% EtOAc in Hexane, KMnO4 active); 1H NMR 300 MHz, CDCl3) δ 7.37-7.28 (m, 5H), 4.52 (s, 2H), 3.60 (t, 2H), 3.49 (t, 2H), 2.37 (s, 1H), 1.69-1.51 (m, 4H), 1.37-1.32 (m, 12H); 13C NMR (151 MHz, CDCl3) δ 138.65, 128.42, 128.35, 127.65, 127.49, 126.89, 72.85, 70.52, 62.78, 32.77, 29.76, 29.58, 29.55, 29.47, 26.20, 25.80; MS (EI) m/z: 264[M]+ (6.5%), 108 (24.9%), 107 (65.6%), 92 (37.8%), 91 (100%); HRMS Calculated: 264.2089. Found: 264.2095.
64%	Stage #1: 1,10-Decanediol With silver(l) oxide In dichloromethane; chloroform at 35℃; for 1h; Stage #2: benzyl bromide for 16h; Inert atmosphere;
60%	Stage #1: 1,10-Decanediol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	1.1 To a 0° C. cooled solution of NaH (5.75 g, 143.67 mmol, 1 eq.) in dry DMF (100 mL), was slowly added compound 1 (25 g, 143.67 mmol, 1 eq.) in dry DMF (150 mL) at 0° C. and the resulting mixture was stirred 1 h at 0° C. After 1 h, benzyl bromide (20.62 ml, 172.41 mmol, 1.2 eq.) was added to the reaction mixture slowly drop-wise over a period of 20 min at 0° C. Then the reaction mixture was stirred at room temp for 12 h. After the completion of the reaction was checked by TLC, the reaction mixture was quenched in ice water and the aqueous layer was extracted with ether (2×30 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude product. The crude was purified by flash column chromatography over silica gel (100-200 mesh) by using 10% ethyl acetate in pet ether as eluent to obtain (23 g, yield-60%) of pure compound.

54%	With silver(l) oxide In dichloromethane; chloroform at 35℃; for 27h; Inert atmosphere;
52%	Stage #1: 1,10-Decanediol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere;
50%	With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 4h;
49%	With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran for 12h; Reflux;
49%	Stage #1: 1,10-Decanediol With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 4h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; Inert atmosphere;
41%	Stage #1: 1,10-Decanediol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 1.5h;	1 C15IMe-acid-2-TG (Int-49) A solution of 1,10-decanediol (1.05 g, 6.00 mmol) in DMF (7 mL)was added dropwise to a suspension of sodium hydride (60% w/w in mineral oil, washed twice with dry petrol, 240 mg, 6.00 mmol) in DMF (8 mL) at 0 °C and the mixture stirred at room temperature for one hour. Benzyl bromide (784 tL, 3.50 mmol) was added dropwise and the mixture stirred at room temperature for 1.5 hours. The reaction was diluted with ethyl acetate (30 mL), quenched with water (20 mL) and the aqueous phase extracted with ethyl acetate (3 x 30 mL). The combined organic extracts washed with water and brine (60 mL each), dried (MgSO4) and concentrated under reduced pressure to give the crude product. Purification by silica gel chromatography (20% to 30% ethyl acetate/hexanes) gave benzyl ether Int-38 (657 mg, 41%) as a colorless oil. ‘H NIVIR (400 IVIFIz, CDC13) 7.39-7.24 (m, 5H), 4.50 (s, 2H), 3.64 (t, J 6.6 Hz, 2H), 3.46 (t, J= 6.7 Hz, 2H), 1.65- 1.52 (m, 4H), 1.40-1.25 (m, 12H).
41%	Stage #1: 1,10-Decanediol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 1.5h;	1 A solution of 1,10-decanediol (1.05 g, 6.00 mmol) in DMF (7 mL) was added dropwise to a suspension of sodium hydride (60% w/w in mineral oil, washed twice with dry petrol, 240 mg, 6.00 mmol) in DMF (8 mL) at 0 °C and the mixture stirred at room temperature for one hour. Benzyl bromide (784 µL, 3.50 mmol) was added dropwise and the mixture stirred at room temperature for 1.5 hours. The reaction was diluted with ethyl acetate (30 mL), quenched with water (20 mL) and the aqueous phase extracted with ethyl acetate (3 × 30 mL). The combined organic extracts washed with water and brine (60 mL each), dried (MgSO4) and chromatography (20% to 30% ethyl acetate/hexanes) gave benzyl ether Int-38 (657 mg, 41%) as a colorless oil. 1H NMR (400 MHz, CDCl3) d 7.39- 7.24 (m, 5H), 4.50 (s, 2H), 3.64 (t, J = 6.6 Hz, 2H), 3.46 (t, J = 6.7 Hz, 2H), 1.65- 1.52 (m, 4H), 1.40- 1.25 (m, 12H).
41%	Stage #1: 1,10-Decanediol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 1.5h;	1 C15bMe-acid-2-TG (Int-49): A solution of 1,10-decanediol (1.05 g, 6.00 mmol) in DMF (7 mL) was added dropwise to a suspension of sodium hydride (60% w/w in mineral oil, washed twice with dry petrol, 240 mg, 6.00 mmol) in DMF (8 mL) at 0 °C and the mixture stirred at room temperature for one hour. Benzyl bromide (784 µL, 3.50 mmol) was added dropwise and the mixture stirred at room temperature for 1.5 hours. The reaction was diluted with ethyl acetate (30 mL), quenched with water (20 mL) and the aqueous phase extracted with ethyl acetate (3 × 30 mL). The combined organic extracts washed with water and brine (60 mL each), dried (MgSO4) and concentrated under reduced pressure to give the crude product. Purification by silica gel chromatography (20% to 30% ethyl acetate/hexanes) gave benzyl ether Int-38 (657 mg, 41%) as a colorless oil. 1H NMR (400 MHz, CDCl3) d 7.39- 7.24 (m, 5H), 4.50 (s, 2H), 3.64 (t, J = 6.6 Hz, 2H), 3.46 (t, J = 6.7 Hz, 2H), 1.65- 1.52 (m, 4H), 1.40- 1.25 (m, 12H).
41%	Stage #1: 1,10-Decanediol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 1.5h;	1 A solution of 1, 10-decanediol (1.05 g, 6.00 mmol) in DMF (7 mL) was added dropwise to a suspension of sodium hydride (60% w/w in mineral oil, washed twice with dry petrol, 240 mg, 6.00 mmol) in DMF (8 mL) at 0 °C and the mixture stirred at room temperature for one hour. Benzyl bromide (784 pL, 3.50 mmol) was added dropwise and the mixture stirred at room temperature for 1.5 hours. The reaction was diluted with ethyl acetate (30 mL), quenched with water (20 mL) and the aqueous phase extracted with ethyl acetate (3 c 30 mL). The combined organic extracts washed with water and brine (60 mL each), dried (MgSCL) and concentrated under reduced pressure to give the crude product. Purification by silica gel chromatography (20% to 30% ethyl acetate/hexanes) gave benzyl ether Int-38 (657 mg, 41%) as a colorless oil. 'H NMR (400 MHz, CDCh) d 7.39 - 7.24 (m, 5H), 4.50 (s, 2H), 3.64 (t, J= 6.6 Hz, 2H), 3.46 (t, J= 6.7 Hz, 2H), 1.65 - 1.52 (m, 4H), 1.40 - 1.25 (m, 12H).
41%	Stage #1: 1,10-Decanediol With sodium hydride In N,N-dimethyl-formamide; mineral oil; Petroleum ether at 0 - 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil; Petroleum ether at 20℃; for 1.5h;	[00447] A solution of 1, 10-decanediol (1.05 g, 6.00 mmol) in DMF (7 mL) was added dropwise to a suspension of sodium hydride (60% w/w in mineral oil, washed twice with dry petrol, 240 mg, 6.00 mmol) in DMF (8 mL) at 0 °C and the mixture stirred at room temperature for one hour. Benzyl bromide (784 pL, 3.50 mmol) was added dropwise and the mixture stirred at room temperature for 1.5 hours. The reaction was diluted with ethyl acetate (30 mL), quenched with water (20 mL) and the aqueous phase extracted with ethyl acetate (3 c 30 mL). The combined organic extracts washed with water and brine (60 mL each), dried (MgSCL) and concentrated under reduced pressure to give the crude product. Purification by silica gel chromatography (20% to 30% ethyl acetate/hexanes) gave benzyl ether Int-38 (657 mg, 41%) as a colorless oil. 'H NMR (400 MHz, CDCh) d 7.39 - 7.24 (m, 5H), 4.50 (s, 2H), 3.64 (t, J= 6.6 Hz, 2H), 3.46 (t, J= 6.7 Hz, 2H), 1.65 - 1.52 (m, 4H), 1.40 - 1.25 (m, 12H).
41%	Stage #1: 1,10-Decanediol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 1.5h;	1 [00384] C15βMe-acid-2-TG (Int-49): [00385] A solution of 1,10-decanediol (1.05 g, 6.00 mmol) in DMF (7 mL) was added dropwise to a suspension of sodium hydride (60% w/w in mineral oil, washed twice with dry petrol, 240 mg, 6.00 mmol) in DMF (8 mL) at 0 °C and the mixture stirred at room temperature for one hour. Benzyl bromide (784 L, 3.50 mmol) was added dropwise and the mixture stirred at room temperature for 1.5 hours. The reaction was diluted with ethyl acetate (30 mL), quenched with water (20 mL) and the aqueous phase extracted with ethyl acetate (3 30 mL). The combined organic extracts washed with water and brine (60 mL each), dried (MgSO4) and concentrated under reduced pressure to give the crude product. Purification by silica gel chromatography (20% to 30% ethyl acetate/hexanes) gave benzyl ether Int-38 (657 mg, 41%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.39 - 7.24 (m, 5H), 4.50 (s, 2H), 3.64 (t, J = 6.6 Hz, 2H), 3.46 (t, J = 6.7 Hz, 2H), 1.65 - 1.52 (m, 4H), 1.40 - 1.25 (m, 12H).
41%	Stage #1: 1,10-Decanediol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 1.5h;	1 [00384] C15βMe-acid-2-TG (Int-49): [00385] A solution of 1,10-decanediol (1.05 g, 6.00 mmol) in DMF (7 mL) was added dropwise to a suspension of sodium hydride (60% w/w in mineral oil, washed twice with dry petrol, 240 mg, 6.00 mmol) in DMF (8 mL) at 0 °C and the mixture stirred at room temperature for one hour. Benzyl bromide (784 L, 3.50 mmol) was added dropwise and the mixture stirred at room temperature for 1.5 hours. The reaction was diluted with ethyl acetate (30 mL), quenched with water (20 mL) and the aqueous phase extracted with ethyl acetate (3 30 mL). The combined organic extracts washed with water and brine (60 mL each), dried (MgSO4) and concentrated under reduced pressure to give the crude product. Purification by silica gel chromatography (20% to 30% ethyl acetate/hexanes) gave benzyl ether Int-38 (657 mg, 41%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.39 - 7.24 (m, 5H), 4.50 (s, 2H), 3.64 (t, J = 6.6 Hz, 2H), 3.46 (t, J = 6.7 Hz, 2H), 1.65 - 1.52 (m, 4H), 1.40 - 1.25 (m, 12H).
40%	With sodium hydride In N,N-dimethyl-formamide at 60℃; for 21h;
	With sodium hydride 1.) THF, 60 deg C, 1 h; 2.) 60-70 deg C, 5 h; Yield given. Multistep reaction;
	With sodium hydride In N,N-dimethyl-formamide
	Stage #1: 1,10-Decanediol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;
	With sodium hydride In tetrahydrofuran at 20℃;
	With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide

Reference： [1]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION - US2013/203829, 2013, A1 Location in patent: Paragraph 0314-0316
[2]Guimond-Tremblay, Jonathan; Gagnon, Marie-Claude; Pineault-Maltais, Jozy-Ann; Turcotte, Vanessa; Auger, Michele; Paquin, Jean-Franois [Organic and Biomolecular Chemistry, 2012, vol. 10, # 6, p. 1145 - 1148]
[3]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES - US2016/207902, 2016, A1 Location in patent: Paragraph 0081-0082
[4]Utsumi, Tatsuki; Noda, Kenta; Kawauchi, Daichi; Ueda, Hirofumi; Tokuyama, Hidetoshi [Advanced Synthesis and Catalysis, 2020, vol. 362, # 17, p. 3583 - 3588]
[5]Sawama, Yoshinari; Masuda, Masahiro; Asai, Shota; Goto, Ryota; Nagata, Saori; Nishimura, Shumma; Monguchi, Yasunari; Sajiki, Hironao [Organic Letters, 2015, vol. 17, # 3, p. 434 - 437]
[6]Shioiri, Takayuki; Irako, Naoko [Tetrahedron, 2000, vol. 56, # 46, p. 9129 - 9142]
[7]Location in patent: scheme or table Muller, Thierry; Heuschling, Paul; Luu, Bang [Synlett, 2009, # 2, p. 217 - 220]
[8]Kondoh, Azusa; Arlt, Alexander; Gabor, Barbara; Fürstner, Alois [Chemistry - A European Journal, 2013, vol. 19, # 24, p. 7731 - 7738]
[9]Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2019/46491, 2019, A1 Location in patent: Paragraph 00463; 00464
[10]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/28787, 2020, A1 Location in patent: Paragraph 00334; 00335
[11]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/176859, 2020, A1 Location in patent: Paragraph 00453-00454
[12]Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2020/176868, 2020, A1 Location in patent: Paragraph 00405; 00462; 00463
[13]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2020/176856, 2020, A1 Location in patent: Paragraph 00446; 00447
[14]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2021/159021, 2021, A1 Location in patent: Paragraph 00384-00385
[15]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2021/159021, 2021, A1 Location in patent: Paragraph 00384-00385
[16]Abe, Junpei; Ding, Feiqing; Greimel, Peter; Guy, Adam T.; Hirabayashi, Yoshio; Ito, Yukishige; Kamiguchi, Hiroyuki [Organic and Biomolecular Chemistry, 2020, vol. 18, # 41, p. 8467 - 8473]
[17]Wanner, Martin J.; Koomen, Gerrit-Jan [European Journal of Organic Chemistry, 1998, # 5, p. 889 - 895]
[18]Shetye, Gauri S.; Singh, Nischal; Jia, Changqing; Nguyen, Chan D.K.; Wang, Guirong; Luk, Yan-Yeung [ChemBioChem, 2014, vol. 15, # 10, p. 1514 - 1523]
[19]Verma, Yogesh Kumar; Reddy, Bonam Srinivasa; Pawar, Mithun S.; Bhunia, Debabrata; Sampath Kumar, Halmuthur M. [ACS Medicinal Chemistry Letters, 2016, vol. 7, # 2, p. 172 - 176]
[20]Xiang, Zheng; Chen, Sheng; Luo, Yongbing; Li, Ping; Zhang, Hailiang [RSC Advances, 2016, vol. 6, # 82, p. 78516 - 78527]
[21]Current Patent Assignee: ALBERTA RES CHEMICALS - WO2020/82162, 2020, A1 Location in patent: Paragraph 0050

34
[ 112-47-0 ]
[ 824-94-2 ]
[ 239115-48-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 1,10-Decanediol With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 0℃; for 1h; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 0 - 20℃; for 21h;
67%	With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran at 50℃; for 48h;
55%	With sodium hydride In N,N-dimethyl-formamide for 6h;

30%

With N-ethyl-N,N-diisopropylamine at 140℃; for 3h; Inert atmosphere; Sealed tube;

6.10 4.3. General procedure method B General procedure: To a microwave vial containing alcohol (7.5-10 mmol) and diisopropylethylamine(9-12 mmol) was added 4-methoxybenzyl chloride (8-16 mmol), the vial sealed under an atmosphere of argon, and heated to 130-150 °C for 3 h. The mixture was poured into saturated aqueous sodium hydrogen carbonate (40 mL) and extracted with ethyl acetate (2x30 mL). The organic extracts were washed with brine (40 mL) and dried over sodium sulfate before being concentrated under reduced pressure. Purification of the residue was carried out by flash chromatography.

Reference： [1]Jaschinski, Tobias; Hiersemann, Martin [Organic Letters, 2012, vol. 14, # 16, p. 4114 - 4117]
[2]Nuruzzaman A, Mohammad; Preston, Thomas C.; Mittler, Silvia; Jones, Nathan D. [Synlett, 2008, # 2, p. 207 - 212]
[3]Hashimoto, Masaru; Liu, Ying; Fang, Kan; Li, Hong-Yu; Campiani, Giuseppe; Nakanishi, Koji [Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 6, p. 1181 - 1194]
[4]Walsh, Katie; Sneddon, Helen F.; Moody, Christopher J. [Tetrahedron, 2014, vol. 70, # 40, p. 7380 - 7387]

35
[ 112-47-0 ]
[ 108-24-7 ]
[ 59694-62-1 ]

Yield	Reaction Conditions	Operation in experiment
49%	With pyridine; dmap In diethyl ether at 20℃; for 17h;	Synthesis of the 10-Acetyloxydecan-1-ol To a stirring solution of 1,10-decanediol (3.4 g, 19.5 mmol) and N,N-dimethylaminopyridine (25 mg, 0.2 mmol) in dry ether (100 mL) was added dropwise acetic anhydride (1.99 g, 19.5 mmol) and pyridine (1.87 g, 23.6 mmol) at 20 °C. This reaction mixture was stirred for 17 h. After then, ether and hydrochloric acid (1 N) was added to the mother liquor and this mixture was extracted with ether. This ether solution was dried with anhydrous Na2SO4 and filtrated. The mother liquor was evaporated and the crude mixture was purified by silica gel chromatography (CHCl3/Et2O = 2/1) to yield the desired compound as white solid in 49 % yield (2.05 g).; m.p. 28.8-29.2 °C; IR (KBr): 718, 892, 969, 1047, 1476, 1743, 2852, 2916, 3447; Rf = 0.60 (CHCl3/Et2O = 2/1); 1H NMR (CDCl3) δ(ppm): 1.19-1.52 (m, 14H), 1.54 (s, 1H), 1.57-1.63 (m, 2H), 2.05 (s, 3H), 3.64 (q, J=6.3 Hz, 2H), 4.05 (t, J=6.8 Hz, 2H); 13C NMR (CDCl3) δ(ppm): 21.03, 25.71, 25.89, 28.59, 29.21, 29.37, 29.41, 29.48, 32.08, 63.09, 64.05, 171.28; MS (EI, 70 eV) m/z (%): 61 (78), 67 (100), 82 (80), 95 (50), 110 (20), 126 (16), 140 (1), 155 (1), 171 (1), 186 (1), 199 (1), 217 (4) [M++H]; Anal: Found: C, 66.44; H, 11.20. Calcd for C12H24O3: C, 66.63; H, 11.18 %.
	With pyridine; dmap In tetrahydrofuran at 0 - 20℃; for 20h;
	With pyridine In N,N-dimethyl-formamide at 20℃;

Reference： [1]Yokoyama, Yasuo; Oyamada, Shun; Suzuki, Junya; Maruyama, Shou; Sakusabe, Takahiro; Suzuki, Shoko [Synthetic Communications, 2018, vol. 48, # 9, p. 1025 - 1032]
[2]Chen, Xin; Millar, Jocelyn G. [Synthesis, 2000, # 1, p. 113 - 118]
[3]Li, Liang-Shi; Jiang, Hongzhou; Messmore, Benjamin W.; Bull, Steve R.; Stupp, Samuel I. [Angewandte Chemie - International Edition, 2007, vol. 46, # 31, p. 5873 - 5876]

36
[ 110-40-7 ]
LiBH₄ [ No CAS ]
[ 112-47-0 ]

Reference： [1]Patent: US2228268,1938,

37
[ 64-17-5 ]
[ 110-40-7 ]
sodium [ No CAS ]
[ 112-47-0 ]

Reference： [1]Patent: US2228268,1938,

38
[ 109-43-3 ]
[ 108-88-3 ]
[ 71-36-3 ]
sodium [ No CAS ]
[ 112-47-0 ]

Reference： [1]Scientific Papers of the Institute of Physical and Chemical Research (Japan),1931,vol. 16,p. 15
Chemisches Zentralblatt,1931,vol. 102,p. 1694

39
[ 7719-09-7 ]
[ 112-47-0 ]
[ 2162-98-3 ]

Reference： [1]Scientific Papers of the Institute of Physical and Chemical Research (Japan),vol. 16,p. 13
Chemisches Zentralblatt,1931,vol. 102,p. 1694

41
[ 112-47-0 ]
[ 116451-83-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In fluorobenzene; dimethyl sulfoxide at 80℃; for 24h;
78%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In fluorobenzene; dimethyl sulfoxide at 85℃; for 24h;

Reference： [1]Nicolaou; Montagnon; Baran; Zhong [Journal of the American Chemical Society, 2002, vol. 124, # 10, p. 2245 - 2258]
[2]Nicolaou; Zhong; Baran [Journal of the American Chemical Society, 2000, vol. 122, # 31, p. 7596 - 7597]

42
[ 112-47-0 ]
[ 76-83-5 ]
[ 38204-88-5 ]

Yield	Reaction Conditions	Operation in experiment
56%	With pyridine; dmap at 20℃; for 48h;
32%	With triethylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	2.2 General synthetic procedure for Series 2 compounds (TPM-G6 - TPM-G10) General procedure: Synthetic procedure for TPM-G6 is described below as a representative example.The same procedure was used for the synthesis of the remaining compounds (TPMG7 - TPM-G10) at similar molar scales. Trityl chloride (697 mg, 2.50 mmol) dissolved in 4 mL of DCM was added to a stirred solution of 1,6-hexanediol (300 mg,2.50 mmol) in DCM at room temperature in a 50 mL round bottom flask undernitrogen atmosphere. Triethylamine (253 mg, 2.50 mmol) diluted in 2 mL of DCMwas added dropwise to the reaction mixture and stirring continued for 24 h at roomtemperature. The reaction mixture was taken in ~30 mL DCM and washed threetimes with water. The organic extract was dried over anhydrous sodium sulfate andconcentrated by rotary evaporation. The crude product was purified by columnchromatography over silica gel 60-120 mesh using petroleum ether/ethyl acetate(9:1) as the eluent to give compound TPM-G6.
	With dmap; triethylamine In dichloromethane at 20℃; for 24h;

Reference： [1]Markidis, Theodoros; Kokotos, George [Journal of Organic Chemistry, 2002, vol. 67, # 5, p. 1685 - 1688]
[2]Singh, Wangkhem P.; Singh, Rajkumar S. [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 138 - 149]
[3]Luo, Yongbing; Chen, Sheng; Zhang, Hailiang [RSC Advances, 2015, vol. 5, # 68, p. 54920 - 54928]

43
[ 112-47-0 ]
[ 58479-61-1 ]
[ 121671-78-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h;
71%	With dmap; triethylamine In dichloromethane at 23℃; for 20h;
56%	With 1H-imidazole In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	2 10-(fert-butyldiphenylsilyloxy)decart-1 -ol (1 ) 10-(fert-butyldiphenylsilyloxy)decart-1 -ol (1 ) Imidazole (3.50 g, 51.7 mmol), followed by TBDPSCI (8.70 g, 31.5 mmol) was added slowly to a solution of 1 ,10-decanediol(5.00 g, 28.7 mmol) in dry THF (60 mL) under 2(9) and left stirring at room temperature for 24 hrs. The reaction was quenched by evaporation of THF in vacuo followed by addition of water (60 mL) and CH2CI2 (60 mL). The organic phase was separated and extracted with water (2 x 50 mL) and washed with brine (50 mL). The organic phase was dried, filtered and concentrated. The crude product was columned [Hexane: EtOAc (9:1)] and pure alcohol obtained as an oil (6.59 g, 56%). Rf = 0.42 (Hexane: EtOAc 8:2).

53%	With dmap; triethylamine In dichloromethane at 22℃; for 20h;
23%	With 1H-imidazole In dichloromethane at 20℃;
	With 1H-imidazole In tetrahydrofuran for 16h;

Reference： [1]La Porta, Elena; Piarulli, Umberto; Cardullo, Francesca; Paio, Alfredo; Provera, Stefano; Seneci, Pierfausto; Gennari, Cesare [Tetrahedron Letters, 2002, vol. 43, # 5, p. 761 - 766]
[2]Tinsley, Jennifer M.; Roush, William R. [Journal of the American Chemical Society, 2005, vol. 127, # 31, p. 10818 - 10819]
[3]Current Patent Assignee: SOUTH AFRICAN NUCLEAR ENERGY CORP LTD; UNIVERSITY OF CAPE TOWN - WO2016/46793, 2016, A2 Location in patent: Page/Page column 32-33
[4]Ponath, Sebastian; Menger, Martina; Grothues, Lydia; Weber, Manuela; Lentz, Dieter; Strohmann, Carsten; Christmann, Mathias [Angewandte Chemie - International Edition, 2018, vol. 57, # 36, p. 11683 - 11687][Angew. Chem., 2018, vol. 130, # 36, p. 11857 - 11861,5]
[5]Yamamoto, Atsushi; Hasui, Keisuke; Matsuo, Hiroshi; Okuda, Katsuhiro; Abe, Masato; Matsumoto, Kenji; Harada, Kazuki; Yoshimura, Yuya; Yamamoto, Takenori; Ohkura, Kazuto; Shindo, Mitsuru; Shinohara, Yasuo [Chemical Biology and Drug Design, 2015, vol. 86, # 5, p. 1304 - 1322]
[6]Flynn, Autumn R.; Mays, Suzanne G.; Ortlund, Eric A.; Jui, Nathan T. [ACS Medicinal Chemistry Letters, 2018, vol. 9, # 10, p. 1051 - 1056]

44
[ 112-47-0 ]
[ 63968-64-9 ]
C₂₅H₄₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: C₁₂H₁₃O₂(CH₃)3(O)(OO) With sodium tetrahydroborate; amberlyst-15 In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 1,10-Decanediol In dichloromethane at 20℃; for 25h;

Reference： [1]Singh, Chandan; Tiwari, Pallavi [Tetrahedron Letters, 2002, vol. 43, # 40, p. 7235 - 7237]

45
[ 112-47-0 ]
[ 57395-49-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With iodine In acetonitrile at 120℃; for 0.0666667h; Microwave irradiation; chemoselective reaction;	4. 2. Typical Procedure for Iodinationof Alcohol General procedure: To a suspension of polymer-bound triphenylphosphine (1.2 mmol) in anhydrous acetonitrile (10 mL) were added iodine (1 mmol) and 1,6-hexanediol diol (1mmol). The reaction mixture was irradiated in microwave reactor at 120 °C for 3 min. The reaction mixture was filtered over a filter paper and washed with chloroform.The filtrate was extracted with aqueous sodium thiosulfate solution and dried with anhydrous sodium sulfate.The reafter, solvent was removed under reduced pressure to obtain 6-iodohexan-1-ol (30) in 93%
78%	With hydrogen iodide In water; toluene at 90℃; for 6h;
45%	Stage #1: 1,10-Decanediol With 1H-imidazole; triphenylphosphine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With iodine In dichloromethane at 20℃; for 3.5h; Inert atmosphere;	10-iododecan-1-ol (13) To an oven dried round bottom flask cooled under Argon is added decane-1,10-diol (1.3 eq, 39mmol) dissolved in 50 mL of anhydrous dichlormethane. The reaction flask is cooled to 0°C where PPh3(1.0 eq, 30 mmol) followed by imidazole (1.5 eq, 45mmol) are added to the reaction vessel. After stirringat 0°C for 10 minutes, iodine (1.0 eq, 30 mmol) is added to the reaction portion wise; after completeaddition, the reaction is stirred for 3.5 hours at room temperature. The reaction was then quenched with10% NH4Cl(aq) and the aqueous layer was extracted 3 × 100 mL of hexanes. The organic layers werecombined, dried with sodium sulfate, and concentrated. The crude reaction product was purified column chromatography by dry-loading with sodium sulfate and using 30% Ethyl Acetate/Hexanes as the mobilephase to afford title compound in 45% yield. 1H NMR (300 MHz, CDCl3) δ 3.61 (t, J = 6.2 Hz, 2H), 3.16 (t, J = 7.0 Hz, 2H), 1.85 - 1.71 (m, 2H), 1.52 (dd, J = 13.7, 6.8 Hz, 2H), 1.42 - 1.11 (m, 14H). 13C NMR(75 MHz, CDCl3) δ 77.65 (s), 77.23 (s), 76.81 (s), 63.25 (s), 33.73 (s), 32.97 (s), 30.69 (s), 29.81 - 29.40(m), 28.71 (s), 25.92 (s), 7.62 (s).

	With hydrogen iodide In toluene at 90℃; for 6h;
	Multi-step reaction with 2 steps 1: 68 percent / 47percent HBr / toluene / Heating 2: 94 percent / NaI / acetone / Ambient temperature
	With hydrogen iodide In water; toluene at 90℃; for 6h;
	Multi-step reaction with 2 steps 1: hydrogen bromide / water; toluene / 48 h / Reflux; Inert atmosphere 2: sodium iodide / acetone / Reflux; Inert atmosphere

Reference： [1]Das, Diparjun; Chanda, Tridib; Rokhum, Lalthazuala [Acta Chimica Slovenica, 2015, vol. 62, # 4, p. 775 - 783]
[2]Muller, Thierry; Coowar, Djalil; Hanbali, Mazen; Heuschling, Paul; Luu, Bang [Tetrahedron, 2006, vol. 62, # 51, p. 12025 - 12040]
[3]Temple, Kayla J.; Wright, Elia N.; Fierke, Carol A.; Gibbs, Richard A. [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3503 - 3507]
[4]Muller, Thierry; Grandbarbe, Luc; Morga, Eleonora; Heuschling, Paul; Luu, Bang [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 24, p. 6023 - 6026]
[5]Abe, Motoji; Hayashikoshi, Takaoki; Kurata, Takeo [Chemistry Letters, 1994, # 10, p. 1789 - 1792]
[6]Location in patent: scheme or table Muller, Thierry; Heuschling, Paul; Luu, Bang [Synlett, 2009, # 2, p. 217 - 220]
[7]Karabiyikoglu, Sedef; Iafe, Robert G.; Merlic, Craig A. [Organic Letters, 2015, vol. 17, # 21, p. 5248 - 5251]

46
[ 112-47-0 ]
[ 2595-90-6 ]
[ 904684-56-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2399 - 2407

47
[ 123-99-9 ]
[ 112-47-0 ]
None [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With molecular sevies 4A In o-xylene for 24h; Heating / reflux;	6 Example 6 [Composition of Polyester] By using the effect of the hafnium (IV) compound as an esterification catalyst, the synthesis of polyester shown in Table 3 was studied (S. R. Sandler and W. Karo, Polymer Synthesis, 2nd ed. (Academic Press: San Diego, 1992) Vol.1, Chapter 2). A Soxhlet tube filled with dried molecular sieves 4A (about 1.5 g) was connected to the top of a 5 ml eggplant flask contained with a teflon coated magnetic stirrer, and a cooling tube was further attached over said Soxhlet tube. 10 mmol of hydroxycarboxylic acid, 2 ml of o-xylene and 0.2 mol % of hafnium chloride (IV)•(THF)2were added and heating reflux was conducted in the argon for 24 hours. After the reaction, a solution wherein the mixture solution was dissolved into 30 ml of chloroform was poured into 150 ml of acetone while being stirred. The white precipitation that was produced, was collected by filtration, and dried under reduced pressure. Furthermore, by the same method, 10 mmol of dicarboxylic acid, 10 mmol of diol, 2 ml of o-xylene and 0.2 mol % of hafnium chloride (IV)•(THF)2 were added and heating reflux was conducted in the argon for 24 hours. After the reaction, the mixture solution was dissolved in 200 ml of chloroform, and 30 ml of methanol was added. The mixture solution was concentrated, the white precipitation thus produced was collected by filtration, and dried under reduced pressure. [0028] The results are shown in Table 3. In Table 3, the following are shown: the yield represents isolated yield; DP stands for the degree of polymerization; DP and the number average molecular weight (Mn) are values obtained by 1H NMR; the weight-average molecular weight (Mw) is the value wherein gel permeation column chromatography (two columns of Two linear TSK-gel-GMXXL (Tosoh Corporation) connected in series were used) is conducted to 0.2% by weight of the generated polymer in THF at 40° C., with polystyrene as a standard; the value in parenthesis for HO [CO(CH2)11O]nH is a value of thermal polymerization condensation in the absence of catalyst; the various values for polyester in the bottom line are the values obtained by using 1 mol % of hafnium chloride (IV)•(THF)2 and conducting the reaction for 4 days. These results revealed that the hafnium chloride (IV)•(THF)2 is useful as a catalyst for polycondensation reaction in the method for preparing polyester using ω-hydroxycarboxylic acid or the method for preparing polyester using α,ω-aliphatic dicarboxylic acid and α, ω-aliphatic diol. [TABLE-US-00003] TABLE 3 isolated yield polyester (%) DPMn × 104 Mw × 104 HO[CO(CH2)9O]nH 95 >200 1.82 3.40 [>3.40]HO[CO(CH2)11O]nH 97 >200 2.77 7.24 [>3.96] (88) (45) -[0.89)] -HO[CO(CH2)2CO2(CH2)6O]nH 98 >200 2.24 3.87 [>4.00]HO[CO(CH2)7CO2(CH2)10O]nH 97 >200 2.69 5.83 [>6.52] 96 >200 1.34 6.51 [>6.09]
96%	With molecular sevies 4A In o-xylene for 24h; Heating / reflux;	6 Example 6 [Composition of Polyester] By using the effect of the hafnium (IV) compound as an esterification catalyst, the synthesis of polyester shown in Table 3 was studied (S. R. Sandler and W. Karo, Polymer Synthesis, 2nd ed. (Academic Press: San Diego, 1992) Vol.1, Chapter 2). A Soxhlet tube filled with dried molecular sieves 4A (about 1.5 g) was connected to the top of a 5 ml eggplant flask contained with a teflon coated magnetic stirrer, and a cooling tube was further attached over said Soxhlet tube. 10 mmol of hydroxycarboxylic acid, 2 ml of o-xylene and 0.2 mol % of hafnium chloride (IV)•(THF)2were added and heating reflux was conducted in the argon for 24 hours. After the reaction, a solution wherein the mixture solution was dissolved into 30 ml of chloroform was poured into 150 ml of acetone while being stirred. The white precipitation that was produced, was collected by filtration, and dried under reduced pressure. Furthermore, by the same method, 10 mmol of dicarboxylic acid, 10 mmol of diol, 2 ml of o-xylene and 0.2 mol % of hafnium chloride (IV)•(THF)2 were added and heating reflux was conducted in the argon for 24 hours. After the reaction, the mixture solution was dissolved in 200 ml of chloroform, and 30 ml of methanol was added. The mixture solution was concentrated, the white precipitation thus produced was collected by filtration, and dried under reduced pressure. [0028] The results are shown in Table 3. In Table 3, the following are shown: the yield represents isolated yield; DP stands for the degree of polymerization; DP and the number average molecular weight (Mn) are values obtained by 1H NMR; the weight-average molecular weight (Mw) is the value wherein gel permeation column chromatography (two columns of Two linear TSK-gel-GMXXL (Tosoh Corporation) connected in series were used) is conducted to 0.2% by weight of the generated polymer in THF at 40° C., with polystyrene as a standard; the value in parenthesis for HO [CO(CH2)11O]nH is a value of thermal polymerization condensation in the absence of catalyst; the various values for polyester in the bottom line are the values obtained by using 1 mol % of hafnium chloride (IV)•(THF)2 and conducting the reaction for 4 days. These results revealed that the hafnium chloride (IV)•(THF)2 is useful as a catalyst for polycondensation reaction in the method for preparing polyester using ω-hydroxycarboxylic acid or the method for preparing polyester using α,ω-aliphatic dicarboxylic acid and α, ω-aliphatic diol. [TABLE-US-00003] TABLE 3 isolated yield polyester (%) DPMn × 104 Mw × 104 HO[CO(CH2)9O]nH 95 >200 1.82 3.40 [>3.40]HO[CO(CH2)11O]nH 97 >200 2.77 7.24 [>3.96] (88) (45) -[0.89)] -HO[CO(CH2)2CO2(CH2)6O]nH 98 >200 2.24 3.87 [>4.00]HO[CO(CH2)7CO2(CH2)10O]nH 97 >200 2.69 5.83 [>6.52] 96 >200 1.34 6.51 [>6.09]

Reference： [1]Current Patent Assignee: JAPAN SCIENCE AND TECHNOLOGY AGENCY - US2004/15005, 2004, A1 Location in patent: Page 6-7
[2]Current Patent Assignee: JAPAN SCIENCE AND TECHNOLOGY AGENCY - US2004/15005, 2004, A1 Location in patent: Page 6-7

48
[ 112-47-0 ]
[ 17435-77-7 ]
[ 752234-97-2 ]

Yield	Reaction Conditions	Operation in experiment
38.9%	With triethylamine In tetrahydrofuran at 20℃; for 40h; Heating / reflux;	2 Example 2; Ethyl 2-[12-hydroxy-2-oxadodecyl]acrylate (3) To a stirred solution of 10 g (57.4 mmol) 1,10-decandiol and 5.86 g (57.90 mmol) triethylamine in 100 ml tetrahydrofurane 8.50 g (57.20 mmol) ethyl α-chloromethylacrylate were added at room temperature. The reaction mixture was refluxed for 40 h. The reaction mixture was cooled down to room temperature and the developing precipitate was filtered off. Evaporation of the filtrate afforded a mixture of a clear, yellow oil with a white solid. This mixture was taken up in a small amount of dichloromethane and filtered again. The filtrate was solved in 150 ml dichloromethane and washed twice with 50 ml water. The organic layer was dried over magnesium sulfate. Then the mixture was filtered, and the solvent was evaporated. The crude product was purified by column chromatography on silica gel with dichloromethane and ethyl acetate as elution agents. This afforded 6,37 g (yield: 38,9 %) of a clear, yellowish oil. IR(film, cm-1) 3425 (OH), 2926/2855 (CH3/CH2), 1714 (CO), 1638 (C=C), 1459/1375/1303 (CH3/CH2), 1270/1172/1102/1031/949.1H-NMR (250 MHz, CDCl3, ppm) 1.08-1.24 (m, 15H, CH2,CH3), 1.24-1.49 (m, 4H, CH2), 3.17 (broad s, 1H, OH), 3.27 (t, 2H, OCH2) 3.37 (t, 2H, OCH2), 3.96 (s, 2H, CH2(1)), 4.01 (q, 2H, OCH2CH3) 5.65 (s, 1H, CH=C), 6.07 (s, 1H, CH=C).13C-NMR (63 MHz, CDCl3, ppm) 13.64 (CH3), 25.36, 25.68, 28.98, 29.07, 29.11, 19.17 and 32.24 (CH2 (4-11)), 60.10 and 61.90 (CH2 (12) and CH2CH3), 68.31 and 70.52 (CH2 (1) and CH2 (3)), 124.69 (C=C-CO), 137.12 (C=C-CO), 165.37 (C=C-CO).
38.9%	With triethylamine In tetrahydrofuran at 20℃; for 40h; Heating / reflux;	2.1 To a stirred solution of 10 g (57.4 mmol) 1,10-decandiol and 5.86 g (57.90 mmol) triethylamine in 100 ml tetrahydrofurane 8.50 g (57.20 mmol) ethyl α-chloromethylacrylate were added at room temperature. The reaction mixture was refluxed for 40 h. The reaction mixture was cooled down to room temperature and the developing precipitate was filtered off. Evaporation of the filtrate afforded a mixture of a clear, yellow oil with a white solid. This mixture was taken up in a small amount of dichloromethane and filtered again. The filtrate was solved in 150 ml dichloromethane and washed twice with 50 ml water. The organic layer was dried over magnesium sulfate the reaction mixture, filtered and evaporated. The raw product was purified by column chromatography on silica gel with dichloromethane and ethyl acetate as eluens. This afforded 6,37 g (yield: 38,9 %) of a clear, yellowish oil. IR(film, cm-1) 3425 (OH), 2926/2855 (CH3/CH2), 1714 (CO), 1638 (C=C), 1459/1375/1303 (CH3/CH2), 1270/1172/1102/1031/949.1H-NMR (250 MHz, CDCl3, ppm) 1.08-1.24 (m, 15H, CH2,CH3), 1.24-1.49 (m, 4H, CH2), 3.17 (broad s, 1 H, OH), 3.27 (t, 2H, OCH2) 3.37 (t, 2H, OCH2), 3.96 (s, 2H, CH2(1)), 4.01 (q, 2H, OCH2CH3) 5.65 (s, 1 H, CH=C), 6.07 (s, 1 H, CH=C).13C-NMR (63 MHz, CDCl3, ppm) 13.64 (CH3), 25.36, 25.68, 28.98, 29.07, 29.11, 19.17 and 32.24 (CH2 (4-11)), 60.10 and 61.90 (CH2 (12) and CH2CH3), 68.31 and 70.52 (CH2 (1) and CH2 (3)), 124.69 (C=C-CO), 137.12 (C=C-CO), 165.37 (C=C-CO).

Reference： [1]Current Patent Assignee: DENTSPLY SIRONA INC - EP1454911, 2004, A1 Location in patent: Page 10
[2]Current Patent Assignee: DENTSPLY SIRONA INC - EP1548021, 2005, A1 Location in patent: Page/Page column 16-17

49
[ 3710-30-3 ]
[ 112-47-0 ]

Yield	Reaction Conditions	Operation in experiment
68%	With H₂; CO In methanol	8 Preparation of 1,10-Decanediol In Methanol EXAMPLE 8 Preparation of 1,10-Decanediol In Methanol In a typical reaction according to the present invention, methanol (75 ml), Rh(CO)2 acac [rhodium (I) acetylacetonate dicarbonyl-commercially available] (18 mg, 0.07 mmol), BISBI (94 mg, 0.17 mmol), and 1,7-octadiene (1.5 g, 14 mmol) were loaded into a 300-ml stirred autoclave. The autoclave was sealed and purged with 50 psi CO/H2 (1:1) at room temperature, then vented and pressurized with 200 psi CO/H2 and heated at 100° C. After reaching 100° C., the autoclave was pressurized to 270 psi with CO/H2. Additional CO/H2 was added throughout the two-hour reaction period in order to maintain a constant temperature and pressure. After the two-hour reaction period and autoclave was cooled to room temperature and opened. A sample was taken for gas chromatographic analysis followed by addition of Raney nickel (2 g) to the autoclave. The above procedure was followed for the hydrogenation step using 1000 psi H2 initial pressure, 100° C., and 2000 psi H2 maintained for three hours. The product as obtained from the autoclave was filtered to remove nickel, and the solvent evaporated to give a white solid. The solid was then recrystallized in ethylene dichloride to give 1.42 g (68% yield) of 1,10-decanediol as identified by NMR and GC mass spectroscopy. Gas chromatographic analysis (DB5 capillary column) of the methanol solution prior to hydrogenation indicated that the ratio of 1,10-decanedialdehyde to all other dialdehydes (by-products) was 15. The dialdehydes were identified by GC mass spectroscopy.

Reference： [1]Current Patent Assignee: EASTMAN CHEMICAL CO - US4742178, 1988, A

50
[ 136918-14-4 ]
[ 112-47-0 ]
[ 161270-70-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 23℃; for 20h;
74%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 23℃; for 20h; Cooling with ice;	[00219] Phthalimide 18. Diisopropyl azodicarboxylate (11.81 mL, 60 mmol, 1.2 equiv) was added slowly to an ice-cooled solution of 1,10-decanediol (17) (26.14 g, 150 mmol, 3.0 equiv), triphenylphosphine (15.73 g, 60 mmol, 1.2 equiv), and phthalimide (7.36 g, 50 mmol, 1.0 equiv) in tetrahydrofuran (125 mL). The resulting yellow solution was stirred at 23 0C for 20 h. The yellow product mixture was concentrated in vacuo and the residue was subjected to flash-column chromatography (hexanes -ethyl acetate, 7:3 to 1: 1), affording the phthalimide 18 (11.28 g, 74%) as a white solid.[00220] R/= 0.30 (hexanes-ethyl acetate 3 :2). 1H NMR (500 MHz, CDCl3), δ 7.84 (dd,2H, J= 5.4, 2.9 Hz), 7.71 (dd, 2H, J= 5.4, 2.9 Hz), 3.68 (t, 2H, J= 7.3 Hz), 3.64 (dd, 2H, J = 12.2, 6.4 Hz), 1.68-1.66 (m, 2H), 1.59-1.53 (m, 2H), 1.33-1.27 (m, 12H). 13C NMR (125MHz, CDCl3), δ 168.7, 134.1, 132.4, 123.4, 63.3, 38.3, 33.0, 29.7, 29.5, 29.3, 28.8, 27.0, 25.9, 22.2. IR (NaCl, thin film), cm"1 3410(br), 2927(m), 2854(m), 1773(m), 1705(s). HRMS-ESI (m/z): [M + H]+ calcd for Ci8H26NO3+, 304.1907; found, 304.1900.
55%	With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere;

With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Cooling with ice;

Reference： [1]Wulff, Jeremy E.; Siegrist, Romain; Myers, Andrew G. [Journal of the American Chemical Society, 2007, vol. 129, # 46, p. 14444 - 14451]
[2]Current Patent Assignee: HARVARD UNIVERSITY - WO2009/20768, 2009, A1 Location in patent: Page/Page column 134
[3]Location in patent: experimental part Pascale, Rossana; Carocci, Alessia; Catalano, Alessia; Lentini, Giovanni; Spagnoletta, Anna; Cavalluzzi, Maria Maddalena; De Santis, Francesco; De Palma, Annalisa; Scalera, Vito; Franchini, Carlo [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 16, p. 5903 - 5914]
[4]Battah, Sinan; Hider, Robert C.; MacRobert, Alexander J.; Dobbin, Paul S.; Zhou, Tao [Journal of Medicinal Chemistry, 2017, vol. 60, # 8, p. 3498 - 3510]

51
[ 112-47-0 ]
[ 112-53-8 ]
paraffin wax C₂₀, C₂₄, C₃₄, C₄₄; methyl branched; mixture of [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,10-Decanediol; 1-dodecyl alcohol at 250℃; Stage #2: With hydrogenchloride In water Stage #3: With hydrogen at 340℃;	2 Condensation of fatty alcohol derived from palm kernel oil and diolC10 diol (1,10-decandiol, 60 g) and C12 primary alcohol (140 g), in molar ratio 1:3 were weighed in a Parr reactor. After that palladium chloride (5 ppm palladium) and 12 g of sodium methoxylate were put in the reactor. Mixing was adjusted to 250 rpm, temperature to 250° C. and pressure to 0.5 MPa. Slight nitrogen purge was maintained to sweep out water liberated in reaction. Condensation reaction was carried out until the amount of condensed alcohol was stabilised in GC analysis. After reaction the product was neutralized with hydrochloric acid, washed with water and dried with calcium chloride.In the next HDO step, the condensed alcohol mixture obtained above was hydrogenated in a high pressure Parr reactor using a dried and activated NiMo/Al2O3 catalyst, to give a methyl branched paraffin. The alcohol was hydrogenated at 340° C., under a pressure of 5 MPa, mixing at 300 rpm until no alcohol peak was detected in the FTIR spectrum. The carbon numbers of the components in the product mixture were C12+C10+C12=C34 with two methyl branches, C12+C12=C24 and C10+C10=C20 with one methyl branch and C12+C10+C10+C12=C44 with three methyl branches. The pour point of soft methyl branched paraffin wax was 18° C. Other properties are given in table 3.

Reference： [1]Current Patent Assignee: NESTE OYJ - US7501546, 2009, B2 Location in patent: Page/Page column 19-20

52
[ 112-47-0 ]
[ 58605-10-0 ]
[ 1174917-31-7 ]

Reference： [1]Chemical Communications,2009,p. 3457 - 3459

53
[ 112-47-0 ]
[ 67-64-1 ]
[ 18650-13-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	In toluene for 12h;	3 Example 3: Substrate Development General procedure: Glove box, α,ω-diol (2.0 mmol), catalyst 2%Ru-6% Na2O/SiO2 (17 mg), acetone (1.162 g, 20.0 mmol) andToluene (4.0 mL) was added in turn to a 50 mL pressure bottle and stirred rapidly for 15 minutes.Seal the pressure bottle, remove the pressure bottle from the glove box and place it in a 100°C oil bath.The reaction was rapidly stirred for 12 hours. After the reaction is over, the pressure bottle is brought to room temperature.The solvent and acetone were removed by rotary evaporation and the target product was isolated by flash column chromatography.
80%	With Mg-Al hydrotalcite; N,N'-Diphenyloxamid; [Cp*₂Ir₂(μ-N,N’-bis(5-tert-butyl-2-methylphenyl)oxalamidato)Cl₂]; calcium hydroxide In isopropyl alcohol at 120℃; for 18h; Autoclave;	1-13; 19-21; 1-5; 40-45 [Example 40] Synthesis of Hexadecane-2,15-dione(effect of N,N’-diphenyl-oxamide Addition) A 100 mE autoclave containing a magnetic stirrer was charged with decane-1,10-diol (5.00 g, 28.7 mmol), hydrotalcite (1.75 g, 35% by mass), calcium hydroxide (1.00 g, 20% by mass), Ir-2 and N,N’-diphenyloxamide, and then purged with nitrogen. Acetone (25 mE, 12 equivalents) and isopropyl alcohol (0.44 mE, 0.2 equivalents) were introduced into the autoclave, followed by initiation of heating and stirring. After stirring at 120° C., the autoclave was cooled. The hydrotalcite and calcium hydroxide were removed by filtration, and the filtrate was analyzed by gas chromatography. The results obtained are shown in Table 3.
77%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine; potassium hydroxide In toluene at 100℃; for 2h; Inert atmosphere;

68%

With [Cp*₂Ir₂(μ-N,N′-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)oxalamidato)Cl₂]; calcium hydroxide In isopropyl alcohol at 140℃; for 32h; Autoclave; Inert atmosphere;

Reference： [1]Current Patent Assignee: WANHUA CHEMICAL GROUP CO LTD - CN107827723, 2018, A Location in patent: Paragraph 0049; 0050; 0051; 0052; 0053; 0054-0058
[2]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - US2021/47254, 2021, A1 Location in patent: Paragraph 0316-0330; 0352-0355; 0482-0488
[3]Location in patent: experimental part Iuchi, Yosuke; Hyotanishi, Megumi; Miller, Brittany E.; Maeda, Kensaku; Obora, Yasushi; Ishii, Yasutaka [Journal of Organic Chemistry, 2010, vol. 75, # 5, p. 1803 - 1806]
[4]Maeda, Hironori; Nara, Hideki; Shimizu, Hideo [Organic Process Research and Development, 2020, vol. 24, # 11, p. 2772 - 2779]

54
[ 67-56-1 ]
[ 112-47-0 ]
[ 2640-94-0 ]
[ 106-79-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 48% 2: 39%	With (2-hydroxyethyl)(methyl)amine; potassium phosphate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In acetone at 25℃; for 24h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Yamamoto, Nobuyuki; Obora, Yasushi; Ishii, Yasutaka [Journal of Organic Chemistry, 2011, vol. 76, # 8, p. 2937 - 2941]

55
[ 112-47-0 ]
[ 106-96-7 ]
[ 68845-58-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: 1,10-Decanediol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 24h;
60%	Stage #1: 1,10-Decanediol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 25℃; for 24h; Inert atmosphere;
50%	Stage #1: 1,10-Decanediol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In tetrahydrofuran at 0 - 20℃; for 24.5h; Inert atmosphere;

44%

With sodium hydride In N,N-dimethyl-formamide; toluene; mineral oil at 20℃; for 18h; Inert atmosphere; Cooling with ice;

Reference： [1]Basak, Dipankar; Christensen, Scott; Surampudi, Sravan K.; Versek, Craig; Toscano, Daniel T.; Tuominen, Mark T.; Hayward, Ryan C.; Venkataraman [Chemical Communications, 2011, vol. 47, # 19, p. 5566 - 5568]
[2]Wang, Kai; Wang, Chun-Yu; Wang, Yun; Li, Hui; Bao, Chun-Yang; Liu, Jian-Yu; Zhang, Sean Xiao-An; Yang, Ying-Wei [Chemical Communications, 2013, vol. 49, # 89, p. 10528 - 10530]
[3]Ranjan, Nihar; Story, Sandra; Fulcrand, Geraldine; Leng, Fenfei; Ahmad, Muzammil; King, Ada; Sur, Souvik; Wang, Weidong; Tse-Dinh, Yuk-Ching; Arya, Dev P. [Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 4904 - 4922]
[4]Fontaine, Devon F. A.; Ivancic, Valerie A.; Reardon, Michael B.; Lazo, Noel D.; Jakobsche, Charles E. [Organic and Biomolecular Chemistry, 2017, vol. 15, # 38, p. 8023 - 8027]

56
[ 112-47-0 ]
[ 58186-27-9 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 673 - 680

57
[ 112-47-0 ]
[ 62-53-3 ]
[ 111797-63-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With Pt-Sn/γ-Al2O3 In o-xylene at 145℃; for 24h; Inert atmosphere;	A general procedure for the direct synthesis of diamines 3 from the N-alkylation of amines 2 with diols 1: General procedure: Under nitrogen atmosphere, to a 15-mL Pyrex glass screw-cap tube were added diol 1 (1.0 mmol), amine 2 (2.0 mmol), Pt-Sn/γ-Al2O3 catalyst (200 mg, 0.5 mol % Pt), and o-xylene (5 mL). The resultant mixture was stirred in the sealed tube at 145 °C for 24 h. After cooled to ambient temperature, the catalyst was removed by centrifugation and washed with CH2Cl2 (3 × 5 mL). The combined supernatant was condensed under reduced pressure and subjected to purification by silica gel column chromatography (eluent: petroleum ether (60-90 °C)/EtOAc = 20:1, v/v), affording diamine 3. The known compounds were identified by comparison of their NMR features with the reported data or of their GC traces with those of the authentic samples. The spectroscopic features of these known compounds are in good agreement with those reported in the literatures. All the new products were characterized by NMR and HRMS techniques.

Reference： [1]Wang, Liandi; He, Wei; Wu, Kaikai; He, Songbo; Sun, Chenglin; Yu, Zhengkun [Tetrahedron Letters, 2011, vol. 52, # 52, p. 7103 - 7107]

58
[ 112-47-0 ]
[ 23160-46-5 ]
[ 646-25-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia;chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II); In toluene; at 155℃; under 33228.3 Torr; for 12h;Autoclave; Inert atmosphere;	Catalyst complex XIVb (for preparation, see below, weighed out under an inert atmosphere), solvent (such an amount that the total solvent volume is 50 ml) and the alcohol to be reacted were placed under an argon atmosphere in a 160 ml Parr autoclave (stainless steel V4A) having a magnetically coupled inclined blade stirrer (stirring speed: 200-500 revolutions/minute). The indicated amount of ammonia was introduced at room temperature either in precondensed form or directly from the pressurized NH3 gas bottle. If hydrogen was used, this was effected by iterative differential pressure metering. The steel autoclave was electrically heated to the temperature indicated and heated for the time indicated while stirring (500 revolutions/minute) (internal temperature measurement). After cooling to room temperature, venting the autoclave and outgassing the ammonia at atmospheric pressure, the reaction mixture was analyzed by GC (30m RTX5 amine 0.32 mm 1.5 mum). Purification of the particular products can, for example, be carried out by distillation. The results for the amination of 1,4-butanediol (table 1a, 1b), diethylene glycol (table 2) and monoethylene glycol (table 3), 2,5-furandimethanol (table 4), alkyldiols (table 5), 1,4-bis(hydroxymethyl)-cyclohexane (table 6) and aminoalcohols (table 7) are given below.
	With ammonia;(carbonyl)chloro(hydrido)tris(triphenylphosphine)ruthenium(II); 1,1,1-tris(diethylphosphinomethyl)ethane; In toluene; at 155℃; under 29252.9 Torr; for 12h;Autoclave;Product distribution / selectivity;	EXAMPLE; General method for the catalytic amination of alcohols by means of ammonia according to the inventionLigand L, metal salt M or catalyst complex XIVb (for preparation, see below, weighed out under an inert atmosphere), solvent and the alcohol to be reacted were placed under an Ar atmosphere in a 160 ml Parr autoclave (stainless steel V4A) having a magnetically coupled inclined blade stirrer (stirring speed: 200-500 revolutions/minute). The indicated amount of ammonia was introduced at room temperature either in precondensed form or directly from the pressurized NH3 gas bottle. If hydrogen was used, this was effected by iterative differential pressure metering. The steel autoclave was electrically heated to the temperature indicated and heated for the time indicated while stirring (500 revolutions/minute) (internal temperature measurement). After cooling to room temperature, venting the autoclave and outgassing the ammonia at atmospheric pressure, the reaction mixture was analyzed by GC (30m RTX5 amine 0.32 mm 1.5 mum). The results for the amination of 1,4-butanediol (tables 1a, 1b and 2), diethylene glycol (tables 3a, 3b and 4), monoethylene glycol (table 5) and diethanolamine (table 6), 1,5-pentanediol, 1,9-nonanediol, 1,6-hexanediol and 1,10-decanediol (table 7) and 2,5-(dimethanol)-furan (table 8) are given below.
	With ammonia;(carbonyl)chloro(hydrido)tris(triphenylphosphine)ruthenium(II); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine]; In toluene; at 155℃; under 29252.9 Torr; for 24h;Inert atmosphere;Product distribution / selectivity;	Ligand L, metal salt M, solvent and the stated alcohol were introduced as initial charge under an Ar atmosphere in a 160 ml Parr autoclave (hte, (stainless steel V4A)) with magnetically coupled slanted-blade stirrer (stirring speed: 200-500 revolutions/minute). The stated amount of ammonia was either precondensed at room temperature or directly metered in from the NH3 pressurized-gas bottle. If hydrogen was used, this was carried out by means of iterative differential pressure metering. The steel autoclave was heated electrically up to the stated temperature and heated (internal temperature measurement) for the stated time with stirring (500 revolutions/minute). After cooling to room temperature, decompressing the autoclave and outgassing the ammonia at atmospheric pressure, the reaction mixture was analyzed by means of GC (30 m RTX5 amine 0.32 mm 1.5 mum). Purification of the particular product can be carried out, for example, by distillation. The results for the amination of octanol (Table 1a and 1b), 1,4-butanediol (Table 2), diethylene glycol (Table 3), 1,9-nonanediol, 1,6-hexanediol, 1,10-decandiol (Table 4) and 1,2-dimethanolfuran (Table 5) are given below:

With (carbonyl)chloro(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine]; In toluene; at 155℃; under 29252.9 Torr; for 24h;Inert atmosphere; Autoclave;

General procedure: Ligand L, see below for the metal salt M or catalyst complex XIVb (manufacturing, inert atmosphere initial mass below), solvent and an alcohol of the reaction, under an argon atmosphere, a magnetic coupling type Parr autoclave of 160ml equipped with atilt wing stirrer (made of special steel V4A) (Stirring speed: were charged to the 200 to 500 rev / min) in. It described theamount of ammonia at room temperature, It is directly metered from the preliminarycondensed with or NH3 gas cylinder. Hydrogenis used Case, this was done by an iterative difference-pressure amount. Power to the temperature indicated the steel autoclave is NetsuNoboru temperature, for a period of time described, has been heated under stirring (500 rev / min) (internal temperature Measurement). The autoclave was cooled to room temperature, depressurized, row outgassing of ammonia at atmospheric pressure after becoming, the reaction mixture was analyzed by GC (30m RTX5 Amin 0.32mm,1.5mum). The amination of 1,4-butanediol result (the first 1a, 1b and the second table), diethylene glycol of the same result (the first 3a, 3b and Table 4), the resultof monoethylene glycol (Table 5), diethanolamine same result (table 6), 1,5-pentanediol, 1,9-nonanediol, 1,6-hexanediol and 1,10-decanediol same result of (table 7), as well as furan-2,5-dimethanol same result (table 8) are as described below.

Reference： [1]Patent: US2012/232293,2012,A1 .Location in patent: Page/Page column 12; 16
[2]Patent: US2012/232294,2012,A1 .Location in patent: Page/Page column 13-14; 19
[3]Patent: US2012/232292,2012,A1 .Location in patent: Page/Page column 10; 13
[4]Angewandte Chemie - International Edition,2012,vol. 51,p. 9156 - 9159
Angew. Chem.,2012,vol. 124,p. 9290 - 9293
[5]Patent: JP2016/27052,2016,A .Location in patent: Paragraph 0088; 0103
[6]Green Chemistry,2018,vol. 20,p. 4591 - 4595

59
[ 112-47-0 ]
[ 57395-46-7 ]

Yield	Reaction Conditions	Operation in experiment
51.3%	With sodium azide; diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 0 - 60℃;	8-azidooctan-1-ol (1-2). To a stirred solution of decane-1,10-diol (1-1, 4.99 g, 34.1 mmol) in DMF (100 mL) was added DBU (7.1 mL, 47.6 mmol), DPPA (6.6 mL, 30.7 mmol), and NaN3 (3.33 g, 51.2 mmol) at 0 ⁰C. The reaction mixture was warmed to room temperature, and then to 60 ⁰C. After being stirred for 10 h, NaN3 (604.1 mg, 9.3 mmol) was added and stirred for another 1 h. The reaction mixture was cooled to room temperature, diluted with EtOAc, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was fractionated by flash column chromatography (SiO2, n-hexane/EtOAc = 1:0 to 20:1) to yield a fraction containing 1-2, which was further purified by flash column chromatography (SiO2, n-hexane/EtOAc = 1:0 to 1:1) to yield 1-2 (2.99 g, 17.5 mmol, 51.3%). 1H NMR (500 MHz, CDCl3) δ 3.63 (t, J = 7.0 Hz, 2H), 3.25 (t, J = 7.0 Hz, 2H), 1.61-1.52 (m, 2H), 1.39-1.32 (m, 8H).

Reference： [1]Otsuki, Satsuki; Nishimura, Shinichi; Takabatake, Hisae; Nakajima, Kozue; Takasu, Yasuaki; Yagura, Toru; Sakai, Yuki; Hattori, Akira; Kakeya, Hideaki [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 6, p. 1608 - 1611]

60
[ 109-65-9 ]
[ 112-47-0 ]
10-(butoxy)decan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: 1,10-Decanediol With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: 1-bromo-butane With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 0℃;	2-(Dodecyloxy)ethanol (10a) General procedure: Ethanediol (1.1 mL, 20.00 mmol) was dissolved in 200 mL anhydrous DMF, NaH (480 mg, 12.0 mmol) was added in at 0°C. The mixture was warmed up to room temperature and stirred for 30 min. Then 1-bromododecane (2.4 mL, 10.00 mmol), TBAI (369 mg, 1.0 mmol) were added in at 0 °C,kept stirring overnight. The reaction mixture was diluted with 20 mL methanol, then washed with 1 N HCl solution, water, saturated aqueous solution of NaHCO3 and brine, successively.The organic phase was dried over Na2SO4, filtered, and then concentrated. The crude mixture was purified by column chromatography (petroleum ether-EtOAc 30 : 1) on silica gel to afford 10a as a colorless oil (1.12 g, 49%).
42%	Stage #1: 1,10-Decanediol With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.166667h; Inert atmosphere; Stage #2: 1-bromo-butane With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide; mineral oil for 3h; Inert atmosphere; Sonication;

Reference： [1]Wang, Guangfa; Bian, Linglin; Zhang, Hui; Wang, Yanhui; Gao, Lijuan; Sun, Kaiyue; Xiang, Lan; Qi, Jianhua [Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 2, p. 161 - 170]
[2]Hussein, Waleed M.; Liu, Tzu-Yu; Maruthayanar, Pirashanthini; Mukaida, Saori; Moyle, Peter M.; Wells, James W.; Toth, Istvan; Skwarczynski, Mariusz [Chemical Science, 2016, vol. 7, # 3, p. 2308 - 2321]

61
[ 112-47-0 ]
[ 93629-15-3 ]
C₂₆H₄₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium hydroxide In ethanol for 15h; Reflux;	3 The 175.7g2,6- methyl-tert-butyl-bromo anisole and 147g1,10- decanediol being added to a 5L three-necked flask, again flask 2L ethanol solvent and 22.6g of sodium hydroxide. The reaction solution was heated at reflux for 15 hours, the heating apparatus was removed, the reaction solution was cooled to 25 . The resulting solid was removed under reduced pressure The solvent was dissolved into 1.5L ether, extracted three times with 1L of distilled water again, the organic layer was extracted once again after the organic layer twice with a dilute hydrochloric acid, dilute aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate 24 hours. The drying agent was removed by filtration pressurized solvent was distilled off the crude solid by column chromatography (developing solvent, chloroform, methanol) to give pure 1,10-decanediol single - (3,5-di-t-butyl, 4- methoxy) anisole 141.5g, 62% yield.
62%	With sodium hydroxide In ethanol for 15h; Reflux;	3 Example 3 175.7 g of 2,6-di-tert-butyl-p-bromomethylanisoleAnd 147 g of 1, 10-decanediol were added to a 5 L three-necked flask,The flask was further charged with 2 L of absolute ethanol solvent and 22.6 g of sodium hydroxide.After the reaction mixture was heated under reflux for 15 hours,Remove the heating device,The reaction was cooled to 25 ° C.After removal of the solvent under reduced pressure, the resulting solid was dissolved in 1.5 L of diethyl ether,Repeated extraction with 1 L of distilled water three times,The organic layer was again extracted twice with dilute sodium bicarbonate solution and dilute hydrochloric acid solution, and the organic layer was dried over anhydrous magnesium sulfate for 24 hours.After removal of the desiccant by filtration, the solvent was removed by distillation under reduced pressure to obtain a solid crude product, which was purified by column chromatography (developing solvent, chloroform, methanol) to give 1,10-decanediol mono- (3,5-di- methoxy) anisole 141.5g, 62% yield.
59%	With sodium hydroxide In ethanol for 6h; Reflux;	4 The 175.7g 2,6-di-tert-butyl to bromine methyl anisole and 154g 1,10- decane diol added to 5L in the three-port flask, then to the flask is added to the flask to 2L anhydrous ethanol solvent and 22.5g sodium hydroxide. Heating to reflux the reaction liquid 6 hours later, heating device removed, cooling the reaction liquid to the 25 °C. After removing the solvent under reduced pressure the obtained solid-dissolving to 1.5L in ether, with 1L distilled water three times repeated extraction, the organic layer with sodium bicarbonate and the dilute solution to the dilute solution of hydrochloric acid after extraction, the organic layer with anhydrous magnesium sulfate drying 12 hours. After filtering to remove the drying agent pressure distillation to remove the solvent to obtain the solid crude product, column chromatography (developing solvent is dichloromethane, methanol) to obtain pure 1,10- decane diol list -(3,5-di-tert-butyl, 4-methoxy) anisole 134.5g, yield 59%

Reference： [1]Current Patent Assignee: CHINA NATIONAL PETROLEUM CORPORATION - CN105732713, 2016, A Location in patent: Paragraph 0108
[2]Current Patent Assignee: CHINA NATIONAL PETROLEUM CORPORATION - CN105732714, 2016, A Location in patent: Paragraph 0121
[3]Current Patent Assignee: CHINA NATIONAL PETROLEUM CORPORATION - CN103319523, 2016, B Location in patent: Paragraph 0080; 0083

62
[ 112-47-0 ]
[ 1643-29-4 ]
bis(3-(4-iodophenyl)propionic acid)decane-1,10-diyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 9147 - 9157

63
[ 112-47-0 ]
[ 1643-29-4 ]
bis(3-(4-iodophenyl)propionic acid)dodecane-1,12-diyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 9147 - 9157

64
[ 112-47-0 ]
[ 112-67-4 ]
10-hydroxydecyl palmitate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In chloroform for 12h; Reflux;	2.1 Preparation of 10-hydroxydecyl palmitate 20.0 g (114.76 mmol) of 1,10-decanediol was dissolved in 600 ml of chloroform at 65 DEG C, and then palmitoyl chloride was added thereto. 17.5 ml (57.38 mmol) was slowly added. The mixture was refluxed for 12 hours And the solvent of the reaction mixture is concentrated until the amount of the solvent remains to about 300 ml. The remaining 1,10-decanediol was removed by filtration. After the filtrate was completely concentrated, the residue was purified by column chromatography (Dichloromethane: Methanol = 50: 1) Separation yielded a white solid compound. (20.9 g, 50.64 mmol, 88% yield).
88%	In chloroform at 65℃; for 12h;	2.1 Step 1. Preparation of 10-hydroxydecyl palmitate 20.0 g (114.76 mmol) of 1,10-decanediol was dissolved in 600 ml of chloroform at 65 and 17.5 ml (57.38 mmol) of palmitoyl chloride was slowly added. The mixture is refluxed for 12 hours, and the reaction mixture is concentrated to about 300 ml. The remaining reaction 1,10-decandiol was removed by filtration. The filtrate was concentrated under reduced pressure. The residue was separated by column chromatography (Dichloromethane: Methanol = 50: 1) to obtain a white solid compound (20.9 g, 50.64 mmol, yield = 88%).

Reference： [1]Current Patent Assignee: NEOPHARM CO.,LTD. - KR101545527, 2015, B1 Location in patent: Paragraph 0081-0082
[2]Current Patent Assignee: NEOPHARM CO.,LTD. - KR2017/103359, 2017, A Location in patent: Paragraph 0078; 0079; 0080

65
[ 112-47-0 ]
[ 1647-16-1 ]
[ 13019-22-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 1-hexadecylcarboxylic acid at 340℃; for 6h; Molecular sieve;	1 A process for the synthesis of 9-decenol, comprising the steps of:1), a 500 mL four-necked flask equipped with a thermometer, a 10 cm rectifying column, a stirring blade, and a heatable dropping funnel equipped with a condenser at the top was charged with 120 g (0.69 mol) of 1,10-decanediol, 0.43mol) palmitic acid, the molar ratio of them is 1.6: 1; and 15gZSM-5 molecular sieve is added.The temperature was raised to 340 ° C, and 1,10-decanediol was continuously fed in a dropwise manner to carry out the reaction.Feeding speed 30g / h, adjust the feed rate, so that consistent with the discharge speed.The reaction was continued for 6 hours, feeding 190 g and discharging about 180 g.The remaining mixture in the four-necked flask can continue as a base material for continuous reaction.2), the material will be atmospheric distillation, by-product 1,9-decadiene and water azeotropic distillation, azeotropic point 99 .The remaining anhydrous material vacuum distillation, collecting 110 ° C / 30mmHg fraction, 9-decenol product, yield 88%, purity 99.4%.

Reference： [1]Current Patent Assignee: HANGZHOU KAIMING PANGDE BIOTECHNOLOGY - CN105330516, 2016, A Location in patent: Paragraph 0035 - 0038

66
[ 112-47-0 ]
[ 76-83-5 ]
1,10-bis(trityloxy)decane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With triethylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	2.3 General synthetic procedure for Series 3 compounds (TPM-G11 - TPMG15) General procedure: Synthetic procedure for TPM-G11 is described below as a representative example.The same procedure was used for the synthesis of the remaining compounds (TPMG12 - TPM-G15) at similar molar scales. Trityl chloride (1.40 g, 5.0 mmol) dissolvedin 6 mL of DCM was added to stirred solution of 1,6-hexanediol (300 mg, 2.50 mmol)in DCM at room temperature in a 50 mL round bottom flask under nitrogenatmosphere. Triethylamine (505 mg, 5.0 mmol) diluted in 2 mL of DCM was addeddropwise to the reaction mixture and stirring continued for 24 h at room temperature.The reaction mixture was taken in ~30 mL DCM and washed three times with water.The organic extract was dried over anhydrous sodium sulfate and concentrated byrotary evaporation. The crude product was purified by column chromatography oversilica gel 60-120 mesh using petroleum ether/ethyl acetate (98:2) as the eluent togive compound TPM-G11.

Reference： [1]Singh, Wangkhem P.; Singh, Rajkumar S. [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 138 - 149]

67
[ 112-47-0 ]
[ 124-09-4 ]
[ 23160-46-5 ]

Yield	Reaction Conditions	Operation in experiment
	With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 155℃; for 24h; Autoclave; Inert atmosphere;	5 general procedure for the amination of alcohols with ammonia according General procedure: The ligand L, the metal salt M, the solvent and the alcohol were introduced as an initial feed into a 160 ml Parr autoclave (hte) having a magnetically coupled tilt blade stirrer (stirring rate: 200 to 500 rpm) in an Ar atmosphere , (Stainless steel V4A)). The amount of ammonia is pre-concentrated at room temperature or directly from a cylinder pressurized with NH3. If hydrogen is used, this is done by adding a repeated differential pressure differential. The steel autoclave was electrically heated to the temperature and heated for the time (internal temperature measurement) with stirring (500 revolutions per minute). After cooling to room temperature, the autoclave was decompressed and ammonia was withdrawn at atmospheric pressure, and the reaction mixture (30 m RTX5 amine 0.32 mml. 5 [mu] [pi]) was analyzed by GC. Purification of a specific product can be carried out, for example, by distillation. Octyl alcohol (Table 1), 1,9-nonanediol, 1,6-hexanediol, 1,10_ The amination results of diols (Table 4) and 2,5-dimethanolfuran (Table 5) are given below.

Reference： [1]Current Patent Assignee: BASF SE - CN103502212, 2016, B Location in patent: Paragraph 0207-0208; 0214

68
[ 112-47-0 ]
[ 85590-00-7 ]

Reference： [1]Patent: CN104151350,2016,B

69
[ 112-47-0 ]
[ 22478-66-6 ]
C₅₀H₇₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In chloroform at 75 - 80℃; for 4.5h;	1 Example 1 Preparation of Compounds of Formula I-1 O.Olmol 1,10-decanediol is dissolved100 ml of chloroform and added to a stirred mixer,In the three-necked flask of the condenser tube,Heating to dissolve,Stirring up to 75-80 ° C,Drip0.02 molDissolved in 100mlChloroform dehydroabiyl chloride,About half an hour drop finished,Continue to constant temperature reaction 4h,After completion of the reaction,The solvent was removed by steaming,Dried in vacuo to give a viscous liquid compound (Formula 1-1)The yield was 94%.[0047] In the same manner as in Example 1,The 1,10-decanediol is replaced with another diol having 4 to 12 carbon atoms (not 10)To give compounds of formula I wherein? Is 2-10 (not 8).

Reference： [1]Current Patent Assignee: BEIJING FORESTRY UNIVERSITY - CN106543004, 2017, A Location in patent: Paragraph 0044; 0045; 0046

70
[ 112-47-0 ]
[ 22478-66-6 ]
C₃₀H₄₈O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In chloroform at 75 - 80℃; for 4.5h;	2.1 1) O.Olmol 1,10-decanediol was dissolved in 100 ml of chloroform and added to a stirrer,In the three-necked flask of the condenser tube,Heating to dissolve,Stirring up to 75-80 ° C,Dropping 0. Olmol of dehydroabiyl chloride dissolved in 100 ml of chloroform,About half an hour drop finished,Continue to constant temperature reaction 4h,After completion of the reaction,The solvent was removed by steaming,Dry in vacuo to give a viscous liquid compound (Formula 7/10)11-0, the yield was 92%

Reference： [1]Current Patent Assignee: BEIJING FORESTRY UNIVERSITY - CN106543004, 2017, A Location in patent: Paragraph 0048'; 0049; 0050; 0051

71
[ 112-47-0 ]
methyl 5-(chlorocarbonyl)furan-2-carboxylate [ No CAS ]
2-(10-hydroxydecyl) 5-methyl furan-2,5-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With 1,4-diaza-bicyclo[2.2.2]octane; triethylamine In tetrahydrofuran at 25℃; for 10h;	6 Preparation of furan dicarboxylic acid sunflower monomethyl ester of formula (4) 10.46 g of decanediol, 8.34 mL of triethylamine and 673 mg of 1,4-diazabicyclo [2.2.2] octane were dissolved in 200 mL of tetrahydrofuran and 5.66 g of monomethyl methanyl monofuranate was added at 25 ° C under the reaction for 10 h after steaming to remove tetrahydrofuran. After adding 30 mL of methylene chloride, the filtrate was filtered to dry the filtrate to give the fumaric acid bisulfate monomethyl ester of the formula (4) in a yield of 94%
	With 1,4-diaza-bicyclo[2.2.2]octane; triethylamine In tetrahydrofuran at 20℃;

Reference： [1]Current Patent Assignee: QINGDAO UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN107098875, 2017, A Location in patent: Paragraph 0071-0073
[2]Shen, Yong; Yao, Binbin; Yu, Guang; Fu, Yao; Liu, Fusheng; Li, Zhibo [Green Chemistry, 2017, vol. 19, # 20, p. 4930 - 4938]

72
1,10-bis(4-methoxybenzyloxy)decane [ No CAS ]
[ 112-47-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite at 20℃; for 18h; Green chemistry; chemoselective reaction;	7.7 4.4 General procedure method C General procedure: To a Reacti-vial (Thermo Scientific) containing the 4-methoxybenzyl protected alcohol (1mmol) were added sodium nitrite (3-10 mol%), glacial acetic acid (1mL) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (1.5-5 mol%). The resulting mixture was stirred at room temperature under an atmosphere of oxygen for 18 h. The solution was then evaporated under reduced pressure and the residue purified by flash chromatography.

Reference： [1]Walsh, Katie; Sneddon, Helen F.; Moody, Christopher J. [Tetrahedron, 2014, vol. 70, # 40, p. 7380 - 7387]

73
[ 112-47-0 ]
[ 317384-91-1 ]
19-(10'-hydroxydecyloxy)-16,19-dioxo-ent-beyerane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	In dichloromethane at 40℃; Inert atmosphere;	General Method for Synthesizing Oxoalcohols 3 and 5. General procedure: A solution of 1 (1 mmol) in SOCl2 (1 mL) was heated at40°C for 2 h. The excess of SOCl2 was distilled at reduced pressure. The residue was treated with anhydrous CH2Cl2 andstirred. The solvent was distilled off. The residue was dried at reduced pressure. The obtained acid chloride of isosteviol (2)was dissolved in anhydrous CH2Cl2 (20 mL), added dropwise to a solution of 1,6-hexanediol (9 mmol) (or 1,10-decanediol)in anhydrous CH2Cl2 (10 mL) under Ar at 40°C, refluxed for 6-10 h, rinsed with H2O (3 10 mL), and dried over CaCl2. Theresidue was chromatographed over silica gel (petroleum ether-EtOAc eluent, 3:1) to afford oxoalcohols 3 and 5 as transparentoils.
57%	Reflux;
50%	In dichloromethane at 40℃; Inert atmosphere;	General Method for Synthesizing Oxoalcohols 3-6. General procedure: A solution of 1 (1 g, 3 mmol) in SOCl2 (1 mL) was heated at40°C for 2 h. The excess of SOCl2 was distilled off at reduced pressure. The residue was treated with anhydrous CH2Cl2 andstirred. The solvent was distilled off. The residue was dried at reduced pressure. The resulting isosteviol acid chloride (2) wasdissolved in anhydrous CH2Cl2 (20 mL) and added dropwise to a solution of the appropriate diol (9 mmol) in anhydrousCH2Cl2 (10 mL) under Ar at 40°C. A solution of the diol (9 mmol) in anhydrous CH2Cl2 (10 mL) under Ar at 40°C was treateddropwise with a solution of the freshly prepared isosteviol acid chloride in anhydrous CH2Cl2 (20 mL). The reaction mixturewas refluxed for 6-10 h, washed with H2O (3 10 mL), dried over CaCl2, and evaporated. The solid was chromatographedover silica gel (eluent petroleum ether-EtOAc, from 10:1 to 3:1) to afford oxoalcohol 3 as an amorphous white powder;oxoalcohols 4-6, as transparent resins.

at 40℃;

Reference： [1]Sharipova; Andreeva; Garifullin; Strobykina, I. Yu.; Strobykina; Voloshina; Kravchenko; Kataev [Chemistry of Natural Compounds, 2018, vol. 54, # 1, p. 92 - 97][Khim. Prir. Soedin., p. 81 - 85,5]
[2]Andreeva, Olga V.; Garifullin, Bulat F.; Sharipova, Radmila R.; Strobykina, Irina Yu.; Sapunova, Anastasiya S.; Voloshina, Alexandra D.; Belenok, Mayya G.; Dobrynin, Alexey B.; Khabibulina, Leysan R.; Kataev, Vladimir E. [Journal of Natural Products, 2020, vol. 83, # 8, p. 2367 - 2380]
[3]Strobykina, I. Yu.; Khaibullin; Sapunova; Voloshina; Sharipova; Kravchenko; Kataev [Chemistry of Natural Compounds, 2018, vol. 54, # 4, p. 688 - 694][Khim. Prir. Soedin., 2018, # 4, p. 583 - 588,6]
[4]Garifullin, Bulat F.; Strobykina, Irina Yu.; Khabibulina, Leysan R.; Sapunova, Anastasiya S.; Voloshina, Aleksandra D.; Sharipova, Radmila R.; Khairutdinov, Bulat I.; Zuev, Yuriy F.; Kataev, Vladimir E. [Natural Product Research, 2021, vol. 35, # 8, p. 1372 - 1378]

74
[ 112-47-0 ]
[ 164200-23-1 ]
C₄₀H₆₂O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	Stage #1: 3α,11α-epoxy-3,4,5,5aα,6,7,8,8a,9,11,11a-undecahydro-3β,6α,9α-trimethylfurano<3,4-j><1,2>benzodioxepin-9β-carboxylic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Stage #2: 1,10-Decanediol In dichloromethane at 20℃;	2 4.2.5. General procedure for the preparation of compounds 6a-l General procedure: Compound 5 (1mmol) was dissolved in 5mL of DCM, EDCI (1.2mmol, 1.2 equiv) and TEA (0.1mmol, 0.1 equiv) were added to the solution respectively. The mixture was stirred for 1h at room temperature then diol was added to the solution. After stirring for 10h, the mixture was diluted with water (5mL) and extracted with EtOAc (3×20mL), then the organic layer was washed with brine, dried (MgSO4) and evaporated. Purification was carried out through column chromatography.

Reference： [1]Zhang, Ning; Yu, Zhimei; Yang, Xiaohong; Hu, Ping; He, Yun [European Journal of Medicinal Chemistry, 2018, vol. 150, p. 829 - 840]

75
[ 112-47-0 ]
[ 141-22-0 ]
C₄₆H₈₆O₆ [ No CAS ]
C₂₈H₅₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With Candida antarctica lipase immobilized on acrylic resin; In toluene; for 9h;Heating; Enzymatic reaction;	General procedure: <strong>[141-22-0]Ricinoleic acid</strong> 1 (R=H) (13mmol) and an excess of diol 2a or 2d (50mmol) was esterified in toluene under vacuum azeotropic distillation for 9h in the presence of C. antarctica lipase. The reaction mixture was cooled, the lipase was filtered off and the solvent was removed under reduced pressure. Diethyl ether was added to the residue, the excess of diol 2 was filtered off and the ether phase was evaporated under vacuum to yield the mixture of esters having about 72% of monoester and 18% of diester (HPLC analysis). The mixture was purified by flash chromatography with silica gel using petroleum ether/diethyl ether/acetic acid: 2/1/0.01 as eluent to give the pure monoesters 3a (n=10) or 3d (n=12). 4.3.1.1.1 Monoester 3a (n=10) 2.24g (60%). FTIR numax (cm-1) 3258 (OH), 3174, 3070 (CH=CH), 2956, 2852, 1735 (carbonylic ester), 1461, 1260, 1177, 1051, 883, 796, 721. 1H NMR (CDCl3, 500MHz) delta ppm 5.56 (1H, m, CH2-CH=CH-CH2-CH(OH)), 5.41 (1H, m, CH2-CH=CH-CH2-CH(OH)), 4.06 (2H, t, J3=7.0Hz, CH2-CH2-O-CO), 3.64 (2H, t, J3=6.5Hz, CH2-OH), 3.62 (1H, m, CH=CH-CH2-CH(OH)), 2.29 (2H, t, J3=7.5Hz, O-CO-CH2-CH2), 2.21 (2H, t, J3=7.0Hz, CH=CH-CH2-CH(OH)), 2.05 (2H, q, J3=7.0Hz, CH2-CH=CH-CH2-CH(OH)), 1.62, 1.47, 1.30 (36H, m, CH2), 0.89 (3H, t, J3=7.0Hz, CH3-CH2). 13C NMR (CDCl3, 125MHz) delta ppm 174.54 (CO), 133.90 (CH2-CH=CH-CH2-CH(OH)), 125.74 (CH2-CH=CH-CH2-CH(OH)), 72.04 (CH=CH-CH2-CH(OH)), 64.92 (CH2-OH), 63.57 (CH2-CH2-O-CO), 35.88 (CH=CH-CH2-CH(OH)), 34.91 (O-CO-CH2-CH2), 27.37 (CH2-CH=CH-CH2-CH(OH)), 37.37 (CH=CH-CH2-CH(OH)-CH2-CH2), 32.36, 30.11, 30.00, 29.89, 29.72, 29.63, 29.15, 26.43, 26.24, 25.51, 23.14 (CH2), 14.60 (CH3-CH2). MS (ESI) positive mode (m/z): calcd for C28H54O4, [M+H]+ 455.4086, found [M+H]+ 455.4036

Reference： [1]Tetrahedron,2015,vol. 71,p. 8557 - 8571

76
[ 93-40-3 ]
[ 112-47-0 ]
decane 1,10-diyl bis(2-(3,4-dimethoxyphenyl)acetate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 24h;	General method for the synthesis of monoesters/diesters A General procedure: To a stirred solution of 3,4-dimethoxyphenylacetic acid (0.19 g, 1.00 mmol) and thecorresponding alcohol (1.00 mmol)/diol (0.50 mmol) in CH2Cl2 (10 mL), 10% DMAP (0.01g, 0.10 mmol) was added and the mixture was cooled to 0°C. Then EDC (0.19 g, 1.00 mmol)was added and the reaction mixture was stirred at 0°C for 30 min and at room temperature for24 hours. Then CH2Cl2 (10 mL) and H2O (10 mL) were added and the organic phase wassuccessively washed with HCl 0.6 N (10 mL), H2O (10 mL), NaHCO3 5% (10 mL), H2O (10mL) and brine (10 mL), dried over Na2SO4 and the volatiles were removed in vacuo. Theresidue was purified with column chromatography using CH2Cl2/MeOH: 9.5/0.5 as eluent

Reference： [1]Pagoni, Aikaterini; Vassiliou, Stamatia [Natural Product Research, 2018, vol. 32, # 11, p. 1267 - 1273]

77
[ 87321-84-4 ]
[ 112-47-0 ]

Yield	Reaction Conditions	Operation in experiment
93.9%	With formic acid; D-glucose; triethylamine; cobalt(II) chloride In dichloromethane at 30℃; for 16.6667h; Inert atmosphere;	3 Example 3 Add 150.0 g of methyl 9,10-epoxydecanoate and 1 ml of a catalyst solution (96.6 mg of CoCl2 dissolved in 1000 ml of dichloromethane, 1 ml of the solution) to the reaction flask.Add 737.2 g of formic acid/triethylamine azeotrope (wherein formic acid)The content is 46.8 wt%,Based on the total mass of formic acid and triethylamine azeotrope) and 2.7 grams of glucose, the flask was replaced with nitrogen three times.React at 30 ° C for 1000 minutes,The conversion of methyl 9,10-epoxydecanoate was 98.6% by gas phase internal standard method and 1H NMR.The selectivity of 1,10-nonanediol is 96.7%.After separation, 122 g of pure 1,10-nonanediol is obtained.Starting from 9,10-epoxymethyl decanoate,The yield of 1,10-nonanediol was 93.9%.

Reference： [1]Current Patent Assignee: WANHUA CHEMICAL GROUP CO LTD - CN108117479, 2018, A Location in patent: Paragraph 0055; 0058; 0059; 0061; 0064; 0067; 0070; 0072

78
[ 112-47-0 ]
[ 105-13-5 ]
[ 239115-48-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With Amberlyst-15 In dichloromethane at 20 - 45℃; for 12h; Inert atmosphere;	10-((4-methoxybenzyl)oxy)decan-1-ol (8) To a stirred solution of 1,10-decanediol (7) (10.0 g, 57.38 mmol) in CH2Cl2 (80 mL), 1.0 g of Amberlyst-15 catalyst (10% w/w) and 4-methoxybenzyl alcohol (5.14 mL, 57.38 mmol) were added sequentially at room temperature. Then, the reaction mixture was heated to reflux at 45 °C for 12 h. After completion of the reaction (monitored by TLC), it was filtered through a Celite pad and residue was washed with CH2Cl2 (2 × 30 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude compound was purified by column chromatography using silica gel (eluted with EtOAc/hexane = 1 : 3) to get the required alcohol 8 (15.19 g, 90%) as a colorless liquid.
82%	With Amberlyst-15 In dichloromethane for 6h; Reflux;	10-((4-Methoxybenzyl)oxy)decan-1-ol (7) To a stirred solution Decane-1,10-diol 6 (6.0 g, 34.48 mmol), p-anisyl alcohol (5.23 g, 37.92 mmol) and catalytic amount (10 % w/w, 1 g) of Amberlyst-15 resin in anhyd CH2Cl2 (75 mL) was refluxed. After 6 h, the crude reaction mixture was filtered and the residue was washed with CH2Cl2 (2 × 50 mL), dried (Na2SO4) and concentrated under reduced pressure to give the crude product which on purification by column chromatography (EtOAc:n-hexane 1:9) furnished the desired alcohol 7 (8.21 g, 82%) as a colorless liquid. IR (neat,): 3413, 3001, 2929, 2855, 1614, 1514, 1248, 1176, 1097, 1038, 822 cm-1. 1H NMR (500 MHz, CDCl3): δ 7.29-7.23 (m, 2H) 6.91-6.82 (m, 2H), 4.43 (s, 2H), 3.80 (s, 3H), 3.60 (t, J = 6.7 Hz, 2H), 3.43 (t, J = 6.7 Hz, 2H), 1.62-1.47 (m, 4H), 1.42-1.20 (m, 12H). 13C NMR (125 MHz, CDCl3): δ 159.0, 130.7, 129.1, 113.6, 72.4, 70.1, 62.9, 55.2, 32.7, 29.6, 29.4, 29.3, 29.3, 26.1, 25.6. HRMS: m/z calcd for C18H30O3Na [M+Na]+: 317.2093; found: 317.2099.

Reference： [1]Kandimalla, Satheeshkumar Reddy; Reddy, B. V. Subba; Sabitha, Gowravaram [Synthetic Communications, 2019, vol. 49, # 22, p. 3191 - 3197]
[2]Sudhakar Reddy, Mopuri; Manikanta, Gembali; Radha Krishna, Palakodety [Tetrahedron Letters, 2019, vol. 60, # 6, p. 504 - 506]

79
[ 112-47-0 ]
C₄₆H₃₂BrN₅O₂ [ No CAS ]
[ 557-34-6 ]
C₁₀₂H₈₀N₁₀O₆Zn₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: 1,10-Decanediol; C₄₆H₃₂BrN₅O₂ With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 80℃; for 24h; Inert atmosphere; Stage #2: zinc diacetate In methanol at 20℃; for 0.5h;	1.5 (5) Synthesis of Compound 8 Under nitrogen protection, 100 mg (0.13 mmol) of bromoporphyrin compound 5 was added to the reaction flask.9.0 mg (0.0165 mmol) DPEphos ligand, 5 mg (0.0055 mmol) Pd2 (dba) 3 catalyst,85 mg (0.26 mmol) of cesium carbonate and 4.9 mg (0.028 mmol) of decanediol were poured into 40 mL of dry toluene, and the mixture was heated to 80 ° C for 24 hours.The solvent was evaporated under reduced pressure.The desiccant was removed by filtration, and 10 mL of a saturated solution of zinc acetate in methanol was added to the filtrate, and the mixture was stirred at room temperature for 30 minutes.The solvent was evaporated under reduced pressure. Water was evaporated.Filtration, distilling off the desiccant under reduced pressure, and the obtained crude product was separated and purified by silica gel column chromatography (eluent: dichloromethane / methanol = 80/1).Recrystallization from dichloromethane/methanol gave 36 mg of red solid, compound 8, yield 77%.

Reference： [1]Current Patent Assignee: NANKAI UNIVERSITY - CN109836430, 2019, A Location in patent: Paragraph 0025-0027; 0043-0046

80
[ 112-47-0 ]
C₁₀H₁₇BrO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96.3%	With oxone; tetrabutylammomium bromide In water at 80℃; for 6h;	1 Add 17.4 g (0.1 mol) of 1,10-decanediol and tetrabutylammonium bromide 74.1 g to a 500 mL single-mouth bottle.(0.23 mol), Oxone 141.4 g (0.23 mol) and 200 ml of water, the mixture was heated to 80 degrees and reacted at this temperature for 6 h. The reaction was examined by TLC (degree of development: petroleum ether / ethyl acetate (volume ratio 1:2), Rf = 0.4). After the reaction is completed, the reaction solution is cooled to about 0 °C, and the precipitated product is filtered and washed with water.After drying, white product II 24.0 g was obtained, yield 96.3%.

Reference： [1]Current Patent Assignee: JIAXING UNIVERSITY - CN109836322, 2019, A Location in patent: Paragraph 0026-0027; 0031-0032; 0034-0035; 0037-0038; 0040

81
[ 112-47-0 ]
[ 621-82-9 ]
decane-1,10-diyl (2E,2′E)-bis(3-phenylacrylate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;	4.8. General Synthetic Procedure for 9g-9i General procedure: A mixture of cinnamic acid (6.30 mmol), EDCI (7.50 mmol), DMAP (0.60 mmol), and anhydrous dichloromethane (20 mL) was stirred to dissolve, then alkane-diol (3 mmol) was added and stirred at room temperature for 12 h. The mixture solution was filtered under reduced pressure. After that, the residue was washed with dichloromethane and water successively, subsequently, purified by preparative TLC eluted with petroleum ether/ethyl acetate = 5:1 to give pale white solid.

Reference： [1]Wang, Jiawen; Hong, Ge; Li, Guoliang; Wang, Wenzhi; Liu, Tianjun [Molecules, 2019, vol. 24, # 24]

82
[ 112-47-0 ]
(5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid [ No CAS ]
1,12-dioxacyclohexacosa-17Z,21Z-diene-13,26-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With hafnium tetrakis(trifluoromethanesulfonate) In toluene at 110℃; for 16h; stereoselective reaction;	General procedure synthesis of macrodiolides. General procedure: Dienedicarboxylic acid (0.2mmol, 1.0 equiv.) and diol (0.2mmol, 1.0 equiv.) were dissolved in toluene (40mL, 5mM). Then Hf(OTf)4 (0.015g, 0.02mmol, 0.1equiv.) was added to the solution and the reaction mixture heated to 110°C for 16-18h. After cooling to room temperature, silica gel (~0.7g) was added and the slurry was concentrated under reduced pressure and purified by column chromatography (elution with petroleum ether/EtOAc (15/1)) to afford the desired product as a colorless oil.

Reference： [1]D'yakonov, Vladimir A.; Dzhemilev, Usein M.; Dzhemileva, Lilya U.; Islamov, Ilgiz I.; Yunusbaeva, Milyausha M. [Bioorganic Chemistry, 2020, vol. 99]

83
[ 112-47-0 ]
(7Z,11Z)-octadeca-7,11-dienedioic acid [ No CAS ]
1,12-dioxacyclotriaconta-19Z,23Z-diene-13,30-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With hafnium tetrakis(trifluoromethanesulfonate) In toluene at 110℃; for 16h; stereoselective reaction;	General procedure synthesis of macrodiolides. General procedure: Dienedicarboxylic acid (0.2mmol, 1.0 equiv.) and diol (0.2mmol, 1.0 equiv.) were dissolved in toluene (40mL, 5mM). Then Hf(OTf)4 (0.015g, 0.02mmol, 0.1equiv.) was added to the solution and the reaction mixture heated to 110°C for 16-18h. After cooling to room temperature, silica gel (~0.7g) was added and the slurry was concentrated under reduced pressure and purified by column chromatography (elution with petroleum ether/EtOAc (15/1)) to afford the desired product as a colorless oil.

Reference： [1]D'yakonov, Vladimir A.; Dzhemilev, Usein M.; Dzhemileva, Lilya U.; Islamov, Ilgiz I.; Yunusbaeva, Milyausha M. [Bioorganic Chemistry, 2020, vol. 99]

84
[ 112-47-0 ]
[ 103-71-9 ]
[ 18653-38-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 2h;	Synthesis of compound C1. General procedure: A solution of triethylene glycol (0.20 mL, 1.497 mmol, 1 equiv) in CH3CN (4 mL) under nitrogen was added phenyl isocyanate (0.41 mL, 3.742 mmol, 2.5 equiv).The mixture was stirred for 15 minutes. DABCO (8.4 mg, 0.075 mmol, 0.05 equiv) or DBU (0.011mL, 0.075 mmol, 0.05 equiv) was added to the above mixture and stirred at room temperature for 2 hours. Then the mixture was concentrated to afford crude product, which was purified by column chromatography using eluent from pure hexanes to 40% EtOAc/hexanes to give the white solid asthe desired product.

Reference： [1]Chen, Anji; Wang, Dan; Samankumara, Lalith P.; Wang, Guijun [Synthesis, 2019, vol. 51, # 15, p. 2897 - 2908]

85
[ 1647-16-1 ]
[ 112-47-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 1,10-decadiene With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 40℃; for 0.0666667h; Stage #2: With dihydrogen peroxide; sodium hydroxide In ethanol; water at 20℃; for 0.0488333h;
69%	Stage #1: 1,10-decadiene With sodium tetrahydroborate; iodine; ethylene dibromide In 1,2-dimethoxyethane at 25℃; for 20h; Stage #2: With dihydrogen peroxide; sodium hydroxide In water at 0 - 25℃; for 0.333333h;	Typical procedure for hydroboration of alkenes with borane from NaBH₄ and I₂ using the PV method (Condition B) General procedure: Iodide (305 mg, 1.2 mmol) and a magnetic stirring bar were placed at the bottom of a test tube (15 mmf × 130 mm), to which 1,2-dibromoethane (0.5 mL) was added slowly to dissolve the iodide. FC-72 (2mL) was added slowly using a syringe. Subsequently, NaBH4 (84 mg, 2.2 mmol), a solution of 4-methylstyrene (1a) (240 mg, 2.0 mmol) in DME (5.0 mL) was added slowly in order, forming four layers. A rubber septum was fitted to the test tube, and a needle equipped with a balloon, which acted asa reservoir of borane gas during the reaction, was then pricked into the septum. The air in the test tube was removed by a syringe until the balloon was completely flattened. The test tube was stirred slowlyfor 20 h at 25 °C, taking care not to mix the layers. The reaction mixture was then cooled to 0 °C withice while stirring. An aqueous NaOH solution (1 M, 1.35 mL) was added slowly in ten portions.Verifying that organic layer was changed to basic condition using a pH test paper, H2O2 solution (30%,0.5 mL) was added slowly in two portion. After 20 min stirring, the organic layer was taken up with aglass pipette to a separating funnel, and washed with water and brine three times. The organic layer was dried over Na2SO4. After filtration, the solvent was evaporated. The residue was then purified by column chromatography on silica gel, eluting hexane/ethyl acetate (8:2) afforded 2-(p-tolyl)-1-ethanol (2a) (172mg, 63%).

Reference： [1]Elsherbini, Mohamed; Huynh, Florence; Dunbabin, Alice; Allemann, Rudolf K.; Wirth, Thomas [Chemistry - A European Journal, 2020, vol. 26, # 50, p. 11423 - 11425]
[2]Soga, Nene; Yoshiki, Tomo; Sato, Aoi; Kawamoto, Takuji; Ryu, Ilhyong; Matsubara, Hiroshi [Tetrahedron Letters, 2021, vol. 69]

86
[ 112-47-0 ]
[ 4481-62-3 ]
[ 538-75-0 ]
decane-1,10-diyl bis[3-oxo-20⁽²⁹⁾-lupen-28-oate] [ No CAS ]
10'-hydroxydecan-1-yl 3-oxo-20⁽²⁹⁾-lupen-28-oate [ No CAS ]
28-N-cyclohexyl-N-[(cyclohexylamino)carbonyl]-3-oxo-20⁽²⁹⁾-lupen-28-oic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 64% 2: 5% 3: 29%	With dmap; 4-(dimethylamino)pyridine hydrochloride In dichloromethane at 0℃; for 24h; Inert atmosphere;	Reaction of betulonic acid (1) with decane-1,10-diol. General procedure: Dicyclohexylacrbodiimide, 0.91 g (4.4 mmol), wasadded to a solution of 2.00 g (4.4 mmol) of betulonicacid (1) in 30 mL of dry CH2Cl2 (Ar, 0°C) and then (i)0.35 g (4.4 mmol) of Py, (ii) 0.05 g (0.44 mmol) DMAP,(iii) 0.05 g (0.44 mmol) DMAP and 0.07 g (0.44 mmol)DMAP·HCl, or (iv) 0.10 g (0.88 mmol) DMAP and0.14 g (0.88 mmol) DMAP·HCl was added under stirring, after which a solution of 0.38 g (2.2 mmol) ofdecane-1,10-diol in 20 mL of dry CH2Cl2 was added. Thereaction mixture was stirred for 24 h and evaporated, andthe residue was subjected to column chromatography(SiO2, PE-MTBE, 5 : 1) to obtain (i) 0.23 g (10%) ofdiester 3, 1.45 g (50%) of urea 5, and 0.95 g (35%)of monoester 4; (ii) 0.51 g (22%) of diester 3, 1.10 g(38%) of urea 5, and 0.72 g (27%) of monoester 4; (iii)0.80 g (35%) of diester 3, 0.75 g (26%) of urea 5, and0.85 g (32%) monoester 4; or (iv) 1.50 g (64%) of diester3, 0.15 g (5%) of urea 5, and 0.78 g (29%) of monoester4.

Reference： [1]Ishmuratov, G. Yu.; Ishmuratova, N. M.; Sayakhov, R. R.; Vydrina, V. A.; Yakovleva, M. P. [Russian Journal of Organic Chemistry, 2021, vol. 57, # 11, p. 1861 - 1867][Zh. Org. Khim., 2021, vol. 57, # 11, p. 1624 - 1632]

87
[ 112-47-0 ]
[ 4481-62-3 ]
decane-1,10-diyl bis[3-oxo-20⁽²⁹⁾-lupen-28-oate] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 6h; Inert atmosphere;	Reaction of betulonic acid (1) with α,ω-dibromides. General procedure: Decane-1,10-diol, 0.60 g (2.0 mmol), or 0.55 g(2.0 mmol) of octane-1,8-diol, or 0.49 g (2.0 mmol) of1,6-dibromohexane was added to a stirred suspensionof 2.00 g (4.4 mmol) of acid 1 and 0.61 g (4.4 mmol)of calcined K2CO3 in 30 mL of dry DMF at roomtemperature under argon. The reaction mixture washeated at 50°C for 6 h and then poured into 100 mL ofcold water, and extracted with CHCl3 (3 × 60 mL). Thecombined extract was washed with water, evaporated,and the residue was subjected to chromatography (SiO2,PE-MTBE, 10 : 1).Decane-1,10-diyl bis[3-oxo-20(29)-lupen-28-oate](3). Yield 1.60 g (76%), Rf 0.9 (PE-MTBE, 2 : 1), whitepowder, mp 167-168°C, [α]D21 +121.0° (c 1.0, CHCl3).1H NMR spectrum (CDCl3), δ, ppm: 0.89 s, 0.92 s,0.94 s, 0.99, 1.03 s (30H, H23-H27), 1.11-2.50 m (64H,CH, pentacyclic core CH2, H2'-H9'), 1.65 s (6H, H30),2.99 d.t (2H, H19, J 10.6, 6.2 Hz), 4.04 t (4H, H1', H10', J5.8 Hz), 4.51 s (2H, H29a), 4.70 s (2H, H29b). 13C NMRspectrum (CDCl3), δ, ppm: 14.60 (CH327), 15.79 (CH326),15.92 (CH325), 19.36 (CH330), 19.62 (CH26), 21.01 (CH324), 21.42 (CH211), 25.51 (CH212), 26.09 (CH23', CH28'), 26.60(CH3, C23), 28.73 (CH22', CH29'), 29.14 (CH25', CH26'),29.44 (CH24', CH27'), 29.58 (CH215), 30.59 (CH216), 32.12(CH221), 33.59 (CH27), 34.11 (CH22), 36.87 (C10), 37.02(CH222), 38.32 (CH13), 39.60 (CH21), 40.61 (C8), 42.43(C14), 46.98 (CH18), 47.29 (C4), 49.28 (CH19), 49.87(CH9), 54.90 (CH5), 56.46 (C17), 63.94 (CH21', CH210'),109.62 (CH229), 150.50 (C20), 176.13 (C28), 218.08 (C3).Mass spectrum (APCI, 20 eV), m/z (Irel, %), Found:1047.8 (50) [M + H]+, 1065.6 (100) [M + H2O]+.Found, %: C 80.30; H 10.51; O 9.19. C70H110O6. Calculated,%: C 80.25; H 10.58; O 9.16. M 1046.83.

88
[ 112-47-0 ]
[ 150841-01-3 ]
[ 4481-62-3 ]
decane-1,10-diyl bis[3-oxo-20⁽²⁹⁾-lupen-28-oate] [ No CAS ]
10'-hydroxydecan-1-yl 3-oxo-20⁽²⁹⁾-lupen-28-oate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 10% 2: 37% 3: 45%	With pyridine In dichloromethane at 0℃; for 10h; Inert atmosphere;	Reaction of betulonic acid chloride (2) withdecane-1,10-diol A solution of 0.38 g (2.2 mmol)of decane-1,10-diol and 0.40 g (5.1 mmol) of Py in20 mL of dry CH2Cl2 was added to 2.08 g (4.4 mmol)of betulonic acid chloride (2), prepared before use bythe procedure in [30], in 40 mL of dry CH2Cl2 (Ar,0°C). The reaction mixture was stirred for 10 h and thendiluted with 100 mL of CH2Cl2, washed with 5% HCl(3 × 30 mL) and saturated solution of NaCl, dried overMgSO4, and evaporated. The residue was subjectedto chromatography (SiO2, PE-MTBE, 5 : 1) to isolate0.23 g (10%) of diester 3, 1.00 g (37%) of mmonoester4, and 0.90 g (45%) of unreacted betulonic acid (1).

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[ CAS No. 112-47-0 ] {[proInfo.proName]}

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[ 112-47-0 ] Synthesis Path-Upstream 1~16

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[ CAS No. 112-47-0 ] {[proInfo.proName]}

Quality Control of [ 112-47-0 ]

Related Doc. of [ 112-47-0 ]

Product Details of [ 112-47-0 ]

Calculated chemistry of [ 112-47-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 112-47-0 ]

Application In Synthesis of [ 112-47-0 ]

[ 112-47-0 ] Synthesis Path-Upstream 1~16

[ 112-47-0 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 112-47-0 ]

Aliphatic Chain Hydrocarbons

Alcohols

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 112-47-0 ]