[ CAS No. 120-47-8 ] {[proInfo.proName]}

Name: 120-47-8|Ethyl 4-hydroxybenzoate|98%
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Quality Control of [ 120-47-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 120-47-8 ]

Product Details of [ 120-47-8 ]

CAS No. :	120-47-8	MDL No. :	MFCD00002353
Formula :	C₉H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NUVBSKCKDOMJSU-UHFFFAOYSA-N
M.W :	166.17	Pubchem ID :	8434
Synonyms :	Ethyl parahydroxybenzoate;Ethyl 4-hydroxybenzoate;NSC 23514	Chemical Name :	Ethyl 4-hydroxybenzoate

Calculated chemistry of [ 120-47-8 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.55
TPSA :	46.53 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) :	-5.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	2.47
Log Po/w (WLOGP) :	1.57
Log Po/w (MLOGP) :	1.64
Log Po/w (SILICOS-IT) :	1.55
Consensus Log Po/w :	1.83

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.6
Solubility :	0.419 mg/ml ; 0.00252 mol/l
Class :	Soluble
Log S (Ali) :	-3.09
Solubility :	0.135 mg/ml ; 0.00081 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.29
Solubility :	0.842 mg/ml ; 0.00507 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.26

Safety of [ 120-47-8 ]

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 [ 120-47-8 ]

* 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 [ 120-47-8 ]
Downstream synthetic route of [ 120-47-8 ]

[ 120-47-8 ] Synthesis Path-Upstream 1~22

1
[ 120-47-8 ]
[ 75-36-5 ]
[ 16357-40-7 ]

Reference： [1] Journal of the Indian Chemical Society, 1955, vol. 32, p. 117

2
[ 120-47-8 ]
[ 24083-13-4 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 22, p. 6225 - 6241

3
[ 120-47-8 ]
[ 3943-89-3 ]

Reference： [1] Journal of the American Chemical Society, 2011, vol. 133, # 44, p. 17630 - 17633

4
[ 120-47-8 ]
[ 110-44-1 ]
[ 64-18-6 ]
[ 473-81-4 ]
[ 3943-89-3 ]
[ 120-80-9 ]
[ 123-31-9 ]
[ 108-95-2 ]
[ 99-96-7 ]

Reference： [1] Journal of Photochemistry and Photobiology A: Chemistry, 2017, vol. 337, p. 62 - 70

5
[ 120-47-8 ]
[ 51934-41-9 ]

Reference： [1] Synlett, 2006, # 6, p. 881 - 884

6
[ 120-47-8 ]
[ 25458-44-0 ]

Reference： [1] Patent: JP2015/516972, 2015, A,

7
[ 120-47-8 ]
[ 3336-41-2 ]

Reference： [1] Gazzetta Chimica Italiana, 1899, vol. 29 I, p. 387,388

8
[ 120-47-8 ]
[ 115-11-7 ]
[ 13205-47-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 41, p. 10745 - 10748[2] Angew. Chem., 2013, vol. 125, # 41, p. 10945 - 10948,4
[3] Patent: US5912258, 1999, A,

9
[ 120-47-8 ]
[ 74-96-4 ]
[ 23676-09-7 ]

Reference： [1] Annales Academiae Scientiarum Fennicae, Series A, 1942, vol. 59, # 9, p. 1,4
[2] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 2, p. 195 - 200
[3] Journal of the Indian Chemical Society, 1999, vol. 76, # 5, p. 246 - 249
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 1272 - 1277
[5] Letters in Drug Design and Discovery, 2014, vol. 11, # 5, p. 628 - 635
[6] Journal of Materials Chemistry C, 2015, vol. 3, # 16, p. 3960 - 3970

10
[ 109-63-7 ]
[ 99-96-7 ]
[ 120-47-8 ]
[ 23676-09-7 ]

Yield	Reaction Conditions	Operation in experiment
38%	at 120℃; for 4 h;	General procedure: In a 50 mL two-necked round-bottomed flask equipped with a magnetic stirring bar, a reflux condenser and a calcium chloride drying tube was placed nicotinic acid (1 g, 8.1 mmol) suspended in boron trifluoride etherate (10 mL). The reaction mixture was stirred and heated to 120 °C overnight during which the creamy reaction mixture changed into a brownish solution. Thin layer chromatography (hexane/ethyl acetate 3:1) revealed complete reaction. The cooled reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (3 x 10 mL). The combined organic extract was washed to the end of effervescence with a saturated solution of NaHCO3. The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo giving a crude yield of 1.11 g (92percent).

Reference： [1] Bulletin of the Chemical Society of Ethiopia, 2018, vol. 32, # 2, p. 387 - 392

11
[ 120-47-8 ]
[ 37470-58-9 ]

Reference： [1] Tetrahedron Letters, 2003, vol. 44, # 13, p. 2729 - 2732

12
[ 120-47-8 ]
[ 213598-07-3 ]

Reference： [1] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263

13
[ 120-47-8 ]
[ 87-66-1 ]
[ 31127-54-5 ]

Yield	Reaction Conditions	Operation in experiment
73.2%	With aluminum (III) chloride In i-Amyl alcohol at 90 - 130℃; for 4.5 h; Inert atmosphere	0.11mol of ethyl p-hydroxybenzoate, 0.1mol of pyrogallic acid, 0.013mol of aluminum trichlorideAnd isoamyl alcohol 450ml mixed in the reactor, the introduction of inert gas, when the system temperature was raised to 90-100 , stop the access,Continue to heat the reaction at 110-130 4.5h, TLC trace to the end of the reaction, the reaction temperature was cooled to 50-60 , incubated 1.5h,Water 150ml was added and the layers were separated. The organic layer was crystallized at 0-5 ° C, filtered and dried to give the product. The molar yield of the product was 73.20percentHPLC ≧ 98.5percent.
70.8%	at 50 - 130℃; for 3.5 h; Inert atmosphere	The acylating agent was 0.11 mol of ethyl p-hydroxybenzoate and 0.1 mol of pyrogallic acid,Concentrated sulfuric acid 0.015 mol was mixed in a reactor,Into the inert gas 30min,When the system temperature rose to 70-80 ,Closed reactorAt 110-130 ,Pressure 0.1-5MPa,Closed reaction 2h,The reaction was cooled to 50-60 ° C,Insulation 1h,Add 20percent ethanol 300ml,Crystallization at 0-5 ,Filter drying,To get the product.The molar yield of the product was 70.80percentHPLC ≥ 98.5percent.

Reference： [1] Patent: CN106365961, 2017, A, . Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046; 0047
[2] Patent: CN106349036, 2017, A, . Location in patent: Paragraph 0044-0049

14
[ 120-47-8 ]
[ 84449-80-9 ]

Reference： [1] Patent: WO2018/144900, 2018, A1,

15
[ 120-47-8 ]
[ 82640-04-8 ]

Reference： [1] Patent: WO2011/47877, 2011, A1,

16
[ 120-47-8 ]
[ 83883-26-5 ]

Reference： [1] Chemical Communications, 2014, vol. 50, # 6, p. 691 - 694
[2] Patent: KR2017/109833, 2017, A,

17
[ 120-47-8 ]
[ 153559-49-0 ]

Reference： [1] Chemistry - A European Journal, 2013, vol. 19, # 10, p. 3504 - 3511

18
[ 120-47-8 ]
[ 109384-19-2 ]
[ 210962-44-0 ]

Yield	Reaction Conditions	Operation in experiment
85.6%	With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 24 h;	Step 1 To a solution of DEAD (12.3 mL, 27.08 mmol)(40percent in toluene)was added to a mixture of ethyl 4-hydroxybenzoate (XIII)(3.0 g, 18.05 mmol), tert-butyl 4-hydroxypiperidine-1-carboxylate (XI)(4.72 g, 23.47 mmol)and triphenylphosphane (6.16 g, 23.47 mmol)in THF (40 mL)at 0° C. The mixture was stirred from 0° C. to room temperature over 1 day before concentrating in vacuo. The residue was diluted with EtOAc, washed with 1 N NaOH and brine, and then evaporated under vacuum. The crude product was purified by chromatography (0→30percent EtOAc/hexanes)to give tert-butyl 4-(4-ethoxycarbonylphenoxy)piperidine-1-carboxylate (XIV)(5.4 g, 15.45 mmol, 85.6percent yield)as a colorless oil. ESIMS found for C₁₉H₂₇NO₅ m/z 372.1 (M+Na).
62%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 24 h;	Reference Example 1:4-[(1-Cyclopentyl-4-piperidinyl)oxy]benzaldehyde (1) Production of tert-butyl 4-[4-(ethoxycarbonyl)phenoxy]tetrahydro-1(2H)-pyridinecarboxylate: Ethyl 4-hydroxybenzoate (4.15 g, 25.0 mmol), tert-butyl 4-hydroxytetrahydro-1(2H)-pyridinecarboxylate (5.0 g, 25.0 mmol) and triphenyl phosphine (7.87 g, 30.0 mmol) were dissolved in tetrahydrofuran (50 mL), and with stirring at 0°C, diisopropyl azodicarboxylate (6.06 g, 30.0 mmol) was added thereto and stirred for 24 hours. The reaction solution was concentrated, and the precipitated white solid was taken out through filtration and washed with ethyl acetate. The mother liquid was washed with aqueous 1 N sodium hydroxide solution and saturated saline water in that order, and the organic layer was dried with magnesium sulfate. The solvent was evaporated off, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate = 9/1) to obtain the intended compound (5.45 g, 62 percent) as a colorless solid.
39%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 16 h;	Step A: tert-Butyl-4-(4-carboxyethylphenyloxy)- 1 -piperidinecarboxylateTo a pre-cooled (0⁰C) suspension of ethyl 4-hydroxybenzoate (10.0 g, 60.2, mmol), 1- tert-butoxycarconyl 4-hydroxypiperidine (12.1 g, 60.1 mmol), and triphenylphosphine (15.8 g, 60.2 mmol) in THF is added diisopropyl azodocarboxylate (11.6 g, 60.1 mmol).The mixture is allowed to come to rt, stirred for 16 h, diluted with ethyl acetate, washed with water, sodium bicarbonate (saturated, aqueous), dried over sodium sulfate, filtered and evaporated in vacuo. The crude product is purified on silica to give the desired product (8.27 g, 39 percent).

Reference： [1] Patent: US2017/313682, 2017, A1, . Location in patent: Paragraph 0702; 0703
[2] Patent: EP1757594, 2007, A1, . Location in patent: Page/Page column 72-73
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 10, p. 1845 - 1857
[4] Patent: WO2007/106705, 2007, A1, . Location in patent: Page/Page column 115

19
[ 120-47-8 ]
[ 109384-19-2 ]
[ 1972-28-7 ]
[ 210962-44-0 ]

Reference： [1] Patent: US2001/56123, 2001, A1,
[2] Patent: EP976722, 2000, A1,
[3] Patent: EP1065200, 2001, A1,
[4] Patent: EP976722, 2000, A1,

20
[ 120-47-8 ]
[ 125248-71-7 ]

Reference： [1] Chemical Communications, 2014, vol. 50, # 6, p. 691 - 694

21
[ 120-47-8 ]
[ 59142-68-6 ]
[ 1196474-68-6 ]

Yield	Reaction Conditions	Operation in experiment
98.8%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 17 h; Inert atmosphere	Bromo-4-fluoro benzaldehyde 10 g (49.26 mmol) and Ethyl 4-hydroxybenzoate 8.19 (49.26 mmol) were mixed in a solution of DMF (50 mL). To this was added potassium carbonate 10.21 g (73.89 mmol). The reaction mixture was stirred at 100° C. (oil bath) for 17 hour under N₂. Cooled to room temperature, mixture of EtOAc and water was added. Stirred for 30 min, concentrated via rotary evaporation to remove most of organic solvent. Filtered, washed with water, dried to get the target molecule, 17 g (98.8percent yield) as white solid. ¹H NMR (DMSO-d₆, 300 MHz) δ ppm 10.13 (s, 1H), 8.03 (d, 2H, J=8.7 Hz) , 7.89 (d, 1H, J=8.7 Hz), 7.45 (m, 1H), 7.26 (d, 2H, J=8.7 Hz), 7.19 (m, 1H), 4.30 (q, 2H) and 1.30 (t, 3H).

Reference： [1] Patent: US2010/256092, 2010, A1, . Location in patent: Page/Page column 76-77
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2533 - 2536

22
[ 120-47-8 ]
[ 1088965-37-0 ]

Reference： [1] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[2] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[3] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[4] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[5] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[6] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263

[ 120-47-8 ] Synthesis Path-Downstream 1~88

1
[ 2568-30-1 ]
[ 120-47-8 ]
4-[1,3]dioxolan-2-ylmethoxy-benzoic acid ethyl ester [ No CAS ]

Reference： [1]Patent: US2680733,1950,

2
[ 120-47-8 ]
[ 59965-20-7 ]
[ 62443-22-5 ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 1254,1255

3
[ 120-47-8 ]
[ 305-80-6 ]
[ 13052-92-1 ]

Reference： [1]Patent: DE111932,

4
[ 120-47-8 ]
[ 5351-23-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrazine hydrate; In ethanol; water;Inert atmosphere; Reflux;	[0739] To a solution of ethyl 4-hydrobenzoate (20 g, 120.35 mmol) in EtOH (60 mL) was added NH2NH2-H2O (88 mL, 1805.4 mmol) under N2 atmosphere. The mixture was stirred overnight at reflux. The mixture was cooled to room temperature, and concentrated under reduced pressure, followed by EtOH trituration, thereby obtaining compound POS-D1-1 (17.54 g, 96%). [0740] 1H NMR (400 Hz, DMSO-d6) delta 9.50 (s, 1H), 7.68 (d, J=8.4 Hz, 2H), 6.78 (d, J=8.8 Hz, 2H), 4.37 (s, 2H). EI-MS m/z: 431 (M++1).
89%	With hydrazine hydrate; In ethanol; water;Reflux;	General procedure: Hydrazides (30-58) were synthesized by one pot conventionalmethod24 Benzoic acid or its derivative (10 mmol) was dissolvedin ethanol (20 mL). Sulfuric acid (3 N, 2 mL) was added and thereaction contents were refluxed for six hours. The reaction wasmonitored with TLC. After the completion of the reaction, the reactionmixture was neutralized by adding solid NaHCO3, and filteredto remove excess of NaHCO3. In the neutralized reaction mixture which contains ethyl ester, hydrazine monohydrate (1.5 mL,3 mmol) was added and refluxed for 3-6 h to complete the reaction.Ethanol and unreacted hydrazine were removed by distillationupto 1/3 volume. The reaction contents were cooled, filteredand recrystallized from methanol to obtain the desired hydrazidecrystals (see Supporting information).
87%	With hydrazine hydrate; In ethanol; for 8h;Reflux;	A solution of methyl ethyl 4-hydroxybenzoate (4) (14.9 g, 90 mmol) and excess of a solutionof hydrazine hydrate (80%) in 20mL of ethanol was heated to reflux during 8 hr. Themixturewas then cooled to room temperature and the solid obtained was filtered, washed with water,and recrystallized from ethanol (yield: 87).

Reference： [1]Patent: US2019/367488,2019,A1 .Location in patent: Paragraph 0738-0740
[2]Patent: WO2020/141459,2020,A1 .Location in patent: Page/Page column 174-175
[3]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6014 - 6024
[4]Molecular Crystals and Liquid Crystals,2016,vol. 631,p. 31 - 46
[5]Journal of the Chemical Society of Pakistan,2016,vol. 38,p. 80 - 90
[6]RSC Advances,2014,vol. 4,p. 58895 - 58901
[7]Journal fur praktische Chemie (Leipzig 1954),1895,vol. <2> 52,p. 234
[8]Journal fur praktische Chemie (Leipzig 1954),1981,vol. 323,p. 360 - 366
[9]Chemical Physics Letters,2007,vol. 435,p. 54 - 58
[10]Journal of Chemical Research,2009,p. 114 - 119
[11]European Journal of Medicinal Chemistry,2009,vol. 44,p. 3340 - 3344
[12]Phosphorus, Sulfur and Silicon and the Related Elements,2010,vol. 185,p. 567 - 572
[13]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 4042 - 4048
[14]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7836 - 7841
[15]Letters in drug design and discovery,2012,vol. 9,p. 135 - 139
[16]Medicinal Chemistry,2012,vol. 8,p. 705 - 710
[17]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2013,vol. 108,p. 100 - 114
[18]Applied Organometallic Chemistry,2013,vol. 27,p. 263 - 268
[19]Monatshefte fur Chemie,2013,vol. 144,p. 825 - 849
[20]European Journal of Medicinal Chemistry,2013,vol. 70,p. 469 - 476
[21]Inorganic Chemistry Communications,2013,vol. 36,p. 199 - 205
[22]European Journal of Medicinal Chemistry,2014,vol. 71,p. 199 - 218
[23]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 134,p. 484 - 492
[24]Phosphorus, Sulfur and Silicon and the Related Elements,2015,vol. 190,p. 1045 - 1055
[25]Supramolecular Chemistry,2015,vol. 27,p. 629 - 641
[26]Asian Journal of Chemistry,2015,vol. 27,p. 3605 - 3608
[27]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3218 - 3230
[28]Polymer,2016,vol. 99,p. 83 - 89
[29]Oriental Journal of Chemistry,2016,vol. 32,p. 2155 - 2161
[30]Journal of the Brazilian Chemical Society,2016,vol. 27,p. 1998 - 2010
[31]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 207 - 212
[32]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 5652 - 5661
[33]Archiv der Pharmazie,2017,vol. 350
[34]Russian Journal of Bioorganic Chemistry,2017,vol. 43,p. 328 - 339
Bioorg. Khim.,2017,vol. 43,p. 328 - 339,12
[35]Patent: CN104892639,2018,B .Location in patent: Paragraph 0065
[36]European Journal of Medicinal Chemistry,2019,vol. 168,p. 1 - 10
[37]Russian Journal of Bioorganic Chemistry,2018,vol. 44,p. 801 - 811
Bioorg. Khim.,2018,vol. 44,p. 801 - 811,11
[38]Inorganica Chimica Acta,2015,vol. 432,p. 213 - 220
[39]Bioorganic Chemistry,2019,vol. 89
[40]Bioorganic Chemistry,2020,vol. 94

5
[ 120-47-8 ]
[ 75-36-5 ]
[ 16357-40-7 ]

Reference： [1]Journal of the Indian Chemical Society,1955,vol. 32,p. 117

6
[ 120-47-8 ]
[ 3685-27-6 ]

Reference： [1]Journal of the Indian Chemical Society,1971,vol. 48,p. 475 - 482

7
[ 120-47-8 ]
[ 3101-60-8 ]
[ 70193-83-8 ]

Reference： [1]Patent: DE2735856,1979,
Chem.Abstr.,1979,vol. 91

8
[ 120-47-8 ]
[ 500-98-1 ]
4-(2-Phenylacetylamino-acetoxy)-benzoic acid ethyl ester [ No CAS ]

Reference： [1]Synthesis,1994,vol. 1,p. 480 - 482

9
[ 120-47-8 ]
[ 1914-65-4 ]
[ 70884-74-1 ]
[ 70884-48-9 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 3968 - 3980

10
[ 120-47-8 ]
[ 3226-34-4 ]
[ 84340-49-8 ]

Reference： [1]Acta Chimica Academiae Scientiarum Hungaricae,1982,vol. 110,p. 117 - 122

11
[ 120-47-8 ]
[ 13421-00-6 ]
[ 82341-38-6 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1065 - 1070

12
[ 120-47-8 ]
[ 52548-63-7 ]
[ 82341-39-7 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1065 - 1070

13
[ 120-47-8 ]
[ 42823-46-1 ]
[ 89022-08-2 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 514 - 519

14
[ 124-38-9 ]
[ 125261-30-5 ]
[ 120-47-8 ]
[ 713-57-5 ]

Reference： [1]European Journal of Organic Chemistry,1998,p. 1811 - 1821
[2]Journal of the Chemical Society. Chemical communications,1992,p. 1729 - 1730

15
[ 56974-61-9 ]
[ 120-47-8 ]
[ 80693-42-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 1595 - 1599

16
[ 120-47-8 ]
[ 4232-27-3 ]
[ 13031-45-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1991,p. 1901 - 1908

17
[ 120-47-8 ]
[ 6429-10-3 ]
4-[2-(4-Ethoxycarbonylphenoxy)ethyl]-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; potassium carbonate; In N-methyl-acetamide;	EXAMPLE 114 4-[2-(4-Ethoxycarbonylphenoxy)ethyl]-1H-imidazole 1.49 g (9 mmol) of ethyl 4-hydroxybenzoate, 251 mg (1.5 mmol) of <strong>[6429-10-3]4-(2-chloroethyl)-1H-imidazole hydrochloride</strong>, 500 g (3.6 mmol) of potassium carbonate and sodium iodide (catalyst) are stirred at 80 C. for 4 days in 5 ml of dimethylformamide. The reaction mixture is cooled and then filtered. The filtrate is evaporated under reduced pressure to give an oily residue. The excess ethyl 4-hydroxybenzoate is extracted with ether at pH=1. The aqueous solution is evaporated under reduced pressure to give the title compound. The latter is purified by preparative high performance chromatography and converted to the oxalate which, after crystallization from an isopropanol/ether mixture, melts at 160-164 C. C14 H16 N2 O3.0.8C2 H2 O4 Elemental analysis: calculated: C 56.4 H 5.34 N 8.4 found: C 56.4 H 5.29 N 8.3

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3806 - 3813
[2]Patent: US5559113,1996,A

18
[ 120-47-8 ]
[ 109384-19-2 ]
[ 210962-44-0 ]

Yield	Reaction Conditions	Operation in experiment
85.6%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 20℃; for 24.0h;	Step 1 To a solution of DEAD (12.3 mL, 27.08 mmol)(40% in toluene)was added to a mixture of ethyl 4-hydroxybenzoate (XIII)(3.0 g, 18.05 mmol), tert-butyl 4-hydroxypiperidine-1-carboxylate (XI)(4.72 g, 23.47 mmol)and triphenylphosphane (6.16 g, 23.47 mmol)in THF (40 mL)at 0 C. The mixture was stirred from 0 C. to room temperature over 1 day before concentrating in vacuo. The residue was diluted with EtOAc, washed with 1 N NaOH and brine, and then evaporated under vacuum. The crude product was purified by chromatography (0→30% EtOAc/hexanes)to give tert-butyl 4-(4-ethoxycarbonylphenoxy)piperidine-1-carboxylate (XIV)(5.4 g, 15.45 mmol, 85.6% yield)as a colorless oil. ESIMS found for C19H27NO5 m/z 372.1 (M+Na).
85.6%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃; for 24.0h;	To a solution of DEAD (12.3 mL, 27.08 mmol) (40% in toluene) was added to a mixture of ethyl 4-hydroxybenzoate (CXI) (3.0 g, 18.05 mmol), tert-butyl 4-hydroxypiperidine-1-carboxylate (CIX) (4.72 g, 23.47 mmol) and triphenylphosphane (6.16 g, 23.47 mmol) in THF (40 mL) at 0 C. The mixture was stirred from 0 C. to room temperature over 1 day before concentrating in vacuo. The residue was diluted with EtOAc, washed with 1 N NaOH and brine, and then evaporated under vacuum. The crude product was purified by chromatography (0→30% EtOAc/hexanes) to give tert-butyl 4-(4-ethoxycarbonylphenoxy)piperidine-1-carboxylate (CXII) (5.4 g, 15.45 mmol, 85.6% yield) as a colorless oil. ESIMS found for C19H27NO5 m/z 372.1 (M+Na).
85.6%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 20℃; for 24.0h;	To a solution of DEAD (12.3 mL, 27.08 mmol) (40% in toluene) was added to a mixture of ethyl 4-hydroxybenzoate (XXXV) (3.0 g, 18.05 mmol), tert-butyl 4-hydroxypiperidine-1-carboxylate (XXXVI) (4.72 g, 23.47 mmol) and triphenylphosphane (6.16 g, 23.47 mmol) in THF (40 mL) at 0 C. The mixture was stirred from 0 C. to room temperature over 1 day before concentrating in vacuo. The residue was diluted with EtOAc, washed with 1 N NaOH and brine, and then evaporated under vacuum. The crude product was purified by chromatography (0→30% EtOAc/hexanes) to give tert-butyl 4-(4-ethoxycarbonylphenoxy)piperidine-1-carboxylate (XXXVII) (5.4 g, 15.45 mmol, 85.6% yield) as a colorless oil. ESIMS found for C19H27NO5 m/z 372.1 (M+Na).

62%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0℃; for 24.0h;	Reference Example 1:4-[(1-Cyclopentyl-4-piperidinyl)oxy]benzaldehyde (1) Production of tert-butyl 4-[4-(ethoxycarbonyl)phenoxy]tetrahydro-1(2H)-pyridinecarboxylate: Ethyl 4-hydroxybenzoate (4.15 g, 25.0 mmol), tert-butyl 4-hydroxytetrahydro-1(2H)-pyridinecarboxylate (5.0 g, 25.0 mmol) and triphenyl phosphine (7.87 g, 30.0 mmol) were dissolved in tetrahydrofuran (50 mL), and with stirring at 0C, diisopropyl azodicarboxylate (6.06 g, 30.0 mmol) was added thereto and stirred for 24 hours. The reaction solution was concentrated, and the precipitated white solid was taken out through filtration and washed with ethyl acetate. The mother liquid was washed with aqueous 1 N sodium hydroxide solution and saturated saline water in that order, and the organic layer was dried with magnesium sulfate. The solvent was evaporated off, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate = 9/1) to obtain the intended compound (5.45 g, 62 %) as a colorless solid.
39%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 16.0h;	Step A: tert-Butyl-4-(4-carboxyethylphenyloxy)- 1 -piperidinecarboxylateTo a pre-cooled (00C) suspension of ethyl 4-hydroxybenzoate (10.0 g, 60.2, mmol), 1- tert-butoxycarconyl 4-hydroxypiperidine (12.1 g, 60.1 mmol), and triphenylphosphine (15.8 g, 60.2 mmol) in THF is added diisopropyl azodocarboxylate (11.6 g, 60.1 mmol).The mixture is allowed to come to rt, stirred for 16 h, diluted with ethyl acetate, washed with water, sodium bicarbonate (saturated, aqueous), dried over sodium sulfate, filtered and evaporated in vacuo. The crude product is purified on silica to give the desired product (8.27 g, 39 %).

Reference： [1]Patent: US2017/313682,2017,A1 .Location in patent: Paragraph 0702; 0703
[2]Patent: US2019/127370,2019,A1 .Location in patent: Paragraph 0972-0973
[3]Patent: US2019/125740,2019,A1 .Location in patent: Paragraph 0551; 0552
[4]Patent: EP1757594,2007,A1 .Location in patent: Page/Page column 72-73
[5]Journal of Medicinal Chemistry,2003,vol. 46,p. 1845 - 1857
[6]Patent: WO2007/106705,2007,A1 .Location in patent: Page/Page column 115

19
[ 120-47-8 ]
[ 37470-58-9 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 2729 - 2732

20
[ 120-47-8 ]
[ 4175-78-4 ]
[ 916796-13-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

21
[ 120-47-8 ]
[ 104618-31-7 ]
[ 952589-02-5 ]

Yield	Reaction Conditions	Operation in experiment
42%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 6h;	4-[4-(1,3-Dioxo-1 , 3-dihydro-isoindol-2-yl)-cyclohexyloxy]-benzoic acid ethyl ester; <n="63"/>To a stirred solution of 2-(4-hydroxycyclohexyl)isoindole-1 ,3-dione (8.0 g, 32.6 mmol) in dry THF (100 ml.) was added triphenyl phosphine (12.8 g, 48.8 mmol) and 4- hydroxy benzoic acid ethyl ester (5.44 g, 32.7 mmol). The reaction mixture was cooled to 0 0C and DIAD (9.6 g, 47.4 mmol) was added dropwise from an addition funnel over a period of 3 h. The reaction was gradually brought to room temperature and stirring continued for 3 h. The solvent was removed under vacuum and ether (100 ml.) was added and cooled to 0 0C. The solid formed was filtered and the clear filtrate concentrated and purified by column chromatography over neutral alumina (8 % AcOEt in hexane) to give 5.13 g (42 %) of 4-[4- (I .S-dioxo-I .S-dihydro-isoindol^-ylJ-cyclohexyloxyJ-benzoic acid ethyl ester. 1H-NMR (300 MHz, CDCI3); delta 1.24 - 1.36 (m, 2H), 1.40 (t, 3H), 1.63 - 1.77 (m, 3H), 2.19 - 2.29 (m, 2H), 2.62 - 2.79 (dq, 2H), 4.15 - 4.72 (m, 1 H), 4.35 (q, 2H), 7.01 (d, 2H), 7.71 (m, 2H), 7.82 (m, 2H), 8.0 (d, 2H). m/z: 394.1 (M+1 )+

Reference： [1]Patent: WO2007/115935,2007,A1 .Location in patent: Page/Page column 61-62

22
[ 120-47-8 ]
[ 99337-98-1 ]
[ 948304-23-2 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3825 - 3840

23
[ 120-47-8 ]
[ 144-48-9 ]
ethyl 4-(carbamoylmethoxy)benzoate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 4577 - 4580
[2]Journal of the American Chemical Society,2010,vol. 132,p. 11110 - 11118

24
[ 120-47-8 ]
[ 62921-76-0 ]
4-(3,6,9,12-tetraoxaheptyloxy)benzoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With 18-crown-6 ether; potassium carbonate; In acetone; for 22h;Reflux;	A mixture of compound ethyl 2,5,8, 11- tetraoxatridecan-13-yl 4-methylbenzenesulfonate (8.1 g, 22.3 mmol), 4- hydroxtybenzoic acid ethyl ester (3.7 g, 22.3 mmol), K2C03 (15.4 g, 111.5 mmol) and 18-crown-6 (0.59 g, 2.2 mmol) was refluxed in acetone (120 ml) for 22 h. The reaction mixture was concentrated and extracted with ethyl acetate. The extract was washed with H20, dried over anhydrous MgS04, and filtrated. The filtrate was evaporated to dryness and the residue was purified by column chromatography on silica gel (dichloromethane/methanol = 100: 1) to obtain the compound (1.93 g, 88%).Yield: 7 g (88%) NMR:1H NMR (400 MHz, CDC13) delta 8.01 - 7.84 (m, 2H), 6.96 - 6.85 (m, 2H), 4.29 (q, J = 7.1 Hz, 2H), 4.12 (dd, J = 5.4, 4.3 Hz, 2H), 3.82 (dd, J= 5.4, 4.2 Hz, 2H), 3.71 - 3.56 (m, 10H), 3.51 - 3.45 (m, 2H), 3.32 (s, 3H), 1.32 (t, J= 7.1 Hz, 3H). 13C{1H} NMR (101 MHz, CDC13) delta 166.29 (s), 162.47 (s), 131.45 (s), 123.01 (s),114.11 (s), 71.90 (s), 70.84 (s), 70.60 (s), 70.59 (s), 70.58 (s), 70.48 (s), 69.51 (s), 67.54 (s), 60.57 (s), 58.98 (s), 14.35 (s).MS(+):[M+Na+]+ = calc. 379.1727, found 379.1743
88%	With 18-crown-6 ether; potassium carbonate; In acetone; for 22h;Reflux;	(JACS, 2007, 129, 13364) A mixture of compound ethyl 2,5,8,11-tetraoxatridecan-13-yl 4-methylbenzenesulfonate (8.1 g, 22.3 mmol), 4-hydroxtybenzoic acid ethyl ester (3.7 g, 22.3 mmol), K2CO3 (15.4 g, 111.5 mmol) and 18-crown-6 (0.59 g, 2.2 mmol) was refluxed in acetone (120 ml) for 22 h. The reaction mixture was concentrated and extracted with ethyl acetate. The extract was washed with H2O, dried over anhydrous MgSO4, and filtrated. The filtrate was evaporated to dryness and the residue was purified by column chromatography on silica gel (dichloromethane/methanol=100:1) to obtain the compound (1.93 g, 88%). Yield: 7 g (88%) NMR: 1H NMR (400 MHz, CDCl3) delta 8.01-7.84 (m, 2H), 6.96-6.85 (m, 2H), 4.29 (q, J=7.1 Hz, 2H), 4.12 (dd, J=5.4, 4.3 Hz, 2H), 3.82 (dd, J=5.4, 4.2 Hz, 2H), 3.71-3.56 (m, 10H), 3.51-3.45 (m, 2H), 3.32 (s, 3H), 1.32 (t, J=7.1 Hz, 3H). 13C{1H} NMR (101 MHz, CDCl3) delta 166.29 (s), 162.47 (s), 131.45 (s), 123.01 (s), 114.11 (s), 71.90 (s), 70.84 (s), 70.60 (s), 70.59 (s), 70.58 (s), 70.48 (s), 69.51 (s), 67.54 (s), 60.57 (s), 58.98 (s), 14.35 (s). NMS (+): [M+Na+]+=calc. 379.1727, found 379.1743
88%	With 18-crown-6 ether; potassium carbonate; In acetone; for 22h;Reflux;	Procedure: (JACS 129 (2007) 13364) A mixture of compound ethyl 2,5,8,11- tetraoxatridecan-13-yl 4-methylbenzenesulfonate (8.1 g, 22.3 mmol), 4- hydroxybenzoic acid ethyl ester (3.7 g, 22.3 mmol), K2C03 (15.4 g, 111.5 mmol) and 18-crown-6 (0.59 g, 2.2 mmol) was refluxed in acetone (120 ml) for 22 h. The reaction mixture was concentrated and extracted with ethyl acetate. The extract was washed with H20, dried over anhydrous MgS04, and filtrated. The filtrate was evaporated to dryness and the residue was purified by column chromatography on silica gel (dichloromethane/methanol = 100:1) to obtain the compound (1.93 g, 88%). Yield: 7 g (88%) NMR: 1H NMR (400 MHz, CDC13) delta 8.01 - 7.84 (m, 2H), 6.96 - 6.85 (m, 2H), 4.29 (q, J = 7.1 Hz, 2H), 4.12 (dd, J= 5.4, 4.3 Hz, 2H), 3.82 (dd, J= 5.4, 4.2 Hz, 2H), 3.71 - 3.56 (m, 10H), 3.51 - 3.45 (m, 2H), 3.32 (s, 3H), 1.32 (t, J= 7.1 Hz, 3H). 13C{1H} NMR (101 MHz, CDC13) delta 166.29 (s), 162.47 (s), 131.45 (s), 123.01 (s), 114.11 (s), 71.90 (s), 70.84 (s), 70.60 (s), 70.59 (s), 70.58 (s), 70.48 (s), 69.51 (s), 67.54 (s), 60.57 (s), 58.98 (s), 14.35 (s). MS(+): [M+Na+]+ = calc. 379.1727, found 379.1743

88%	With 18-crown-6 ether; potassium carbonate; In acetone; for 22h;Reflux;	Procedure: (JACS 129 (2007) 13364) A mixture of compound ethyl 2,5,8,11- tetraoxatridecan-13-yl 4-methylbenzenesulfonate (8.1 g, 22.3 mmol), 4- hydroxybenzoic acid ethyl ester (3.7 g, 22.3 mmol), K2C03 (15.4 g, 111.5 mmol) and 18-crown-6 (0.59 g, 2.2 mmol) was refluxed in acetone (120 ml) for 22 h. The reaction mixture was concentrated and extracted with ethyl acetate. The extract was washed with H20, dried over anhydrous MgS04, and filtrated. The filtrate was evaporated to dryness and the residue was purified by column chromatography on silica gel (dichloromethane/methanol = 100:1) to obtain the compound (1.93 g, 88%). Yield: 7 g (88%) NMR: 1H NMR (400 MHz, CDC13) delta 8.01 - 7.84 (m, 2H), 6.96 - 6.85 (m, 2H), 4.29 (q, J = 7.1 Hz, 2H), 4.12 (dd, J= 5.4, 4.3 Hz, 2H), 3.82 (dd, J= 5.4, 4.2 Hz, 2H), 3.71 - 3.56 (m, 10H), 3.51 - 3.45 (m, 2H), 3.32 (s, 3H), 1.32 (t, J= 7.1 Hz, 3H). 13C{1H} NMR (101 MHz, CDC13) delta 166.29 (s), 162.47 (s), 131.45 (s), 123.01 (s), 114.11 (s), 71.90 (s), 70.84 (s), 70.60 (s), 70.59 (s), 70.58 (s), 70.48 (s), 69.51 (s), 67.54 (s), 60.57 (s), 58.98 (s), 14.35 (s). MS(+): [M+Na+]+ = calc. 379.1727, found 379.1743
88%	With 18-crown-6 ether; potassium carbonate; In acetone; for 22h;Reflux;	Procedure: (JACS 129 (2007) 13364) A mixture of compound ethyl 2,5,8,11- tetraoxatridecan-13-yl 4-methylbenzenesulfonate (8.1 g, 22.3 mmol), 4- hydroxybenzoic acid ethyl ester (3.7 g, 22.3 mmol), K2C03 (15.4 g, 111.5 mmol) and 18-crown-6 (0.59 g, 2.2 mmol) was refluxed in acetone (120 ml) for 22 h. The reaction mixture was concentrated and extracted with ethyl acetate. The extract was washed with H20, dried over anhydrous MgS04, and filtrated. The filtrate was evaporated to dryness and the residue was purified by column chromatography on silica gel (dichloromethane/methanol = 100:1) to obtain the compound (1.93 g, 88%). Yield: 7 g (88%) NMR: 1H NMR (400 MHz, CDC13) delta 8.01 - 7.84 (m, 2H), 6.96 - 6.85 (m, 2H), 4.29 (q, J = 7.1 Hz, 2H), 4.12 (dd, J= 5.4, 4.3 Hz, 2H), 3.82 (dd, J= 5.4, 4.2 Hz, 2H), 3.71 - 3.56 (m, 10H), 3.51 - 3.45 (m, 2H), 3.32 (s, 3H), 1.32 (t, J= 7.1 Hz, 3H). 13C{1H} NMR (101 MHz, CDC13) delta 166.29 (s), 162.47 (s), 131.45 (s), 123.01 (s), 114.11 (s), 71.90 (s), 70.84 (s), 70.60 (s), 70.59 (s), 70.58 (s), 70.48 (s), 69.51 (s), 67.54 (s), 60.57 (s), 58.98 (s), 14.35 (s). MS(+): [M+Na+]+ = calc. 379.1727, found 379.1743
88%	With 18-crown-6 ether; potassium carbonate; In acetone; for 22h;Reflux;	Synthesis of 4-PEG4-benzoic Acid Ethyl Ester Procedure: (JACS, 2007, 129, 13364) A mixture of compound ethyl 2,5,8,11-tetraoxatridecan-13-yl 4-methylbenzenesulfonate (8.1 g, 22.3 mmol), 4-hydroxybenzoic acid ethyl ester (3.7 g, 22.3 mmol), K2CO3 (15.4 g, 111.5 mmol) and 18-crown-6 (0.59 g, 2.2 mmol) was refluxed in acetone (120 ml) for 22 h. The reaction mixture was concentrated and extracted with ethyl acetate. The extract was washed with H2O, dried over anhydrous MgSO4, and filtrated. The filtrate was evaporated to dryness and the residue was purified by column chromatography on silica gel (dichloromethane/methanol=100:1) to obtain the compound (1.93 g, 88%). Yield: 7 g (88%) NMR: 1H NMR (400 MHz, CDCl3) delta 8.01-7.84 (m, 2H), 6.96-6.85 (m, 2H), 4.29 (q, J=7.1 Hz, 2H), 4.12 (dd, J=5.4, 4.3 Hz, 2H), 3.82 (dd, J=5.4, 4.2 Hz, 2H), 3.71-3.56 (m, 10H), 3.51-3.45 (m, 2H), 3.32 (s, 3H), 1.32 (t, J=7.1 Hz, 3H). 13C{1H} NMR (101 MHz, CDCl3) delta 166.29 (s), 162.47 (s), 131.45 (s), 123.01 (s), 114.11 (s), 71.90 (s), 70.84 (s), 70.60 (s), 70.59 (s), 70.58 (s), 70.48 (s), 69.51 (s), 67.54 (s), 60.57 (s), 58.98 (s), 14.35 (s). MS(+): [M+Na+]+=calc. 379.1727, found 379.1743
88%	With 18-crown-6 ether; potassium carbonate; In acetone; for 22h;Reflux;	(JACS, 2007, 129, 13364) A mixture of compound ethyl 2,5,8,11-tetraoxatridecan-13-yl 4-methylbenzenesulfonate (8.1 g, 22.3 mmol), 4-hydroxybenzoic acid ethyl ester (3.7 g, 22.3 mmol), K2CO3 (15.4 g, 111.5 mmol) and 18-crown-6 (0.59 g, 2.2 mmol) was refluxed in acetone (120 ml) for 22 h. The reaction mixture was concentrated and extracted with ethyl acetate. The extract was washed with H2O, dried over anhydrous MgSO4, and filtrated. The filtrate was evaporated to dryness and the residue was purified by column chromatography on silica gel (dichloromethane/methanol=100:1) to obtain the compound (1.93 g, 88%). 10144] Yield:10145] 7 g (88%)10146] NMR:10147] ?H NMR (400 MHz, CDC13) oe 8.01-7.84 (m, 2H),6.96-6.85 (m, 2H), 4.29 (q, J=7.1 Hz, 2H), 4.12 (dd, J=5.4, 4.3Hz, 2H), 3.82 (dd, J=5.4, 4.2 Hz, 2H), 3.71-3.56 (m, 1OH),3.51-3.45 (m, 2H), 3.32 (s, 3H), 1.32 (t, J=7.1 Hz, 3H).10148] ?3C{?H} NMR (101 MHz, CDC13) oe 166.29 (s),162.47 (s), 131.45 (s), 123.01 (s), 114.11(s), 71.90(s), 70.84(s), 70.60 (s), 70.59 (s), 70.58 (s), 70.48 (s), 69.51 (s), 67.54(s), 60.57 (s), 58.98 (s), 14.35 (s).10149] MS(+):10150] [M+Na]=calc. 379.1727. found 379.1743
	With 18-crown-6 ether; potassium carbonate; In acetone; for 22h;Reflux;	Synthesis of 4-PEG4-benzoic Acid Ethyl Ester Procedure: (JACS, 2007, 129, 13364) A mixture of compound ethyl 2,5,8,11-tetraoxatridecan-13-yl 4-methylbenzenesulfonate (8.1 g, 22.3 mmol), 4-hydroxybenzoic acid ethyl ester (3.7 g, 22.3 mmol), K2CO3 (15.4 g, 111.5 mmol) and 18-crown-6 (0.59 g, 2.2 mmol) was refluxed in acetone (120 ml) for 22 h. The reaction mixture was concentrated and extracted with ethyl acetate. The extract was washed with H2O, dried over anhydrous MgSO4, and filtrated. The filtrate was evaporated to dryness and the residue was purified by column chromatography on silica gel (dichloromethane/methanol=100:1) to obtain the compound (1.93 g, 88%). Yield: 7 g (88%) NMR: 1H NMR (400 MHz, CDCl3) delta 8.01-7.84 (m, 2H), 6.96-6.85 (m, 2H), 4.29 (q, J=7.1 Hz, 2H), 4.12 (dd, J=5.4, 4.3 Hz, 2H), 3.82 (dd, J=5.4, 4.2 Hz, 2H), 3.71-3.56 (m, 10H), 3.51-3.45 (m, 2H), 3.32 (s, 3H), 1.32 (t, J=7.1 Hz, 3H). 13C{1H} NMR (101 MHz, CDCl3) delta 166.29 (s), 162.47 (s), 131.45 (s), 123.01 (s), 114.11 (s), 71.90 (s), 70.84 (s), 70.60 (s), 70.59 (s), 70.58 (s), 70.48 (s), 69.51 (s), 67.54 (s), 60.57 (s), 58.98 (s), 14.35 (s). MS(+): [M+Na+]+=calc. 379.1727, found 379.1743
	With 18-crown-6 ether; potassium carbonate; In acetone; for 22h;Reflux;	Synthesis of 4-PEG4-benzoic acid ethyl ester Procedure: [0191] (JACS, 2007, 129, 13364) A mixture of compound ethyl 2,5,8,11-tetraoxatridecan-13-yl 4-methylbenzenesulfonate (8.1 g, 22.3 mmol), 4-hydroxybenzoic acid ethyl ester (3.7 g, 22.3 mmol), K2CO3 (15.4 g, 111.5 mmol) and 18-crown-6 (0.59 g, 2.2 mmol) was refluxed in acetone (120 ml) for 22 h. The reaction mixture was concentrated and extracted with ethyl acetate. The extract was washed with H2O, dried over anhydrous MgSO4, and filtrated. The filtrate was evaporated to dryness and the residue was purified by column chromatography on silica gel (dichloromethane/methanol=100:1) to obtain the compound (1.93 g, 88%). Yield: [0192] 7 g (88%) NMR: [0193] 1H NMR (400 MHz, CDCl3) delta 8.01-7.84 (m, 2H), 6.96-6.85 (m, 2H), 4.29 (q, J=7.1 Hz, 2H), 4.12 (dd, J=5.4, 4.3 Hz, 2H), 3.82 (dd, J=5.4, 4.2 Hz, 2H), 3.71-3.56 (m, 10H), 3.51-3.45 (m, 2H), 3.32 (s, 3H), 1.32 (t, J=7.1 Hz, 3H). [0194] 13C{1H} NMR (101 MHz, CDCl3) delta 166.29 (s), 162.47 (s), 131.45 (s), 123.01 (s), 114.11 (s), 71.90 (s), 70.84 (s), 70.60 (s), 70.59 (s), 70.58 (s), 70.48 (s), 69.51 (s), 67.54 (s), 60.57 (s), 58.98 (s), 14.35 (s). MS(+): [0195] [M+Na+]+=calc. 379.1727. found 379.1743

Reference： [1]Patent: WO2012/107419,2012,A1 .Location in patent: Page/Page column 21-22
[2]Patent: US2013/323719,2013,A1 .Location in patent: Paragraph 0079-0083
[3]Patent: WO2014/19711,2014,A1 .Location in patent: Page/Page column 44; 45
[4]Patent: WO2014/19710,2014,A1 .Location in patent: Page/Page column 27
[5]Patent: WO2014/19707,2014,A2 .Location in patent: Page/Page column 39; 40
[6]Patent: US2015/147752,2015,A1 .Location in patent: Paragraph 0238-0243
[7]Patent: US2015/148536,2015,A1 .Location in patent: Paragraph 0142 - 0150
[8]Journal of the American Chemical Society,2007,vol. 129,p. 13364 - 13365
[9]Patent: US2015/147750,2015,A1 .Location in patent: Paragraph 0219-0225
[10]Patent: US2015/147751,2015,A1 .Location in patent: Paragraph 0191-0195

25
[ 120-47-8 ]
[ 2312-15-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: K₂CO₃ 2: Acid hydrolysis
	Multi-step reaction with 2 steps 1: sodium ethylate; ethanol 2: ethanolic KOH-solution
	Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 5 h / Reflux 2: hydrogenchloride; water / ethanol / 5 h / Reflux

	Multi-step reaction with 2 steps 1: potassium carbonate 2: potassium hydroxide
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide 2: sodium hydroxide; ethanol
	Multi-step reaction with 2 steps 1: potassium carbonate / acetone 2: potassium hydroxide; hydrogenchloride / ethanol; water
	Multi-step reaction with 2 steps 1: potassium carbonate; potassium iodide / 48 h / Reflux 2: potassium hydroxide / ethanol / 7 h / Reflux
	Multi-step reaction with 2 steps 1: potassium carbonate; potassium iodide / butanone 2: potassium hydroxide / ethanol
	Multi-step reaction with 2 steps 1: potassium carbonate / butanone / 24 h / Reflux 2: sodium hydroxide / ethanol; water / 12 h / Reflux
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / Reflux 2: potassium hydroxide / ethanol / Reflux

Reference： [1]Petrenko, Alexey; Goodby, John W. [Journal of Materials Chemistry, 2007, vol. 17, # 8, p. 766 - 782]
[2]Pierce; Salsbury; Fredericksen [Journal of the American Chemical Society, 1942, vol. 64, p. 1691,1692]
[3]Koh, Teck Ming; Ha, Sie Tiong; Lee, Teck Leong; Lee, Siew Ling; Yeap, Guan Yeow; Lin, Hong Cheu; Subramaniam, Ramesh T. [Chinese Chemical Letters, 2011, vol. 22, # 5, p. 619 - 622]
[4]Wang, Li; Liu, Xiao-Jun; Huang, Ping; Gong, Qing-Ping; Li, Yong-Hong; Wang, Bi-Qin; Zhao, Ke-Qing [Molecular Crystals and Liquid Crystals, 2011, vol. 541, p. 53 - 59]
[5]Gruzdev; Akopova; Frolova [Russian Journal of General Chemistry, 2013, vol. 83, # 4, p. 652 - 658][Zh. Obshch. Khim., 2013, vol. 83, # 4, p. 564 - 570,7]
[6]Koh, Teck-Ming; Ha, Sie-Tiong; Yeap, Guan-Yeow; Lin, Hong-Cheu [Chinese Chemical Letters, 2013, vol. 24, # 10, p. 926 - 928]
[7]Singh, Sachin Kumar; Singh, Hemant Kumar; Nandi, Rajib; Kumar, Vijay; Tarcea, Nicolae; Popp, Jürgen; Singh, Ranjan K.; Singh, Bachcha [Polyhedron, 2014, vol. 74, p. 99 - 112]
[8]Kanth, Priyanka; Singh, Hemant Kumar; Kumar, Vijay; Singh, Sachin Kumar; Rao, D.S. Shankar; Prasad, S. Krishna; Singh, Bachcha [Journal of Molecular Liquids, 2019, vol. 289]
[9]Balkanli, Emine; Çakar, Fatih; Ocak, Hale; Cankurtaran, Özlem; Bilgin Eran, Belkız [Turkish Journal of Chemistry, 2021, vol. 45, # 1, p. 71 - 81]
[10]Bhat S, Vanishree; Kumar, Sandeep; Raghunathan, V. A. [Journal of Molecular Liquids, 2021, vol. 340]

26
[ 120-47-8 ]
[ 115595-27-2 ]

Reference： [1]Journal of Materials Chemistry,2007,vol. 17,p. 766 - 782
[2]Macromolecules,2012,vol. 45,p. 5556 - 5566
[3]Asian Journal of Chemistry,2016,vol. 28,p. 1270 - 1274
[4]Angewandte Chemie - International Edition,2022,vol. 61
Angew. Chem.,2022,vol. 134

27
[ 120-47-8 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 81 percent / K₂CO₃ / ethanol / Heating 2: 82 percent / NaOH / H₂O; ethanol / Heating
	Multi-step reaction with 2 steps 1: alcoholic KOH-solution / 120 - 130 °C / Destillation des Reaktionsprodukts 2: aqueous potash
	Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 10 h / 85 °C / Reflux 2: potassium hydroxide / ethanol; water / 5 h / 105 °C / Reflux

	Multi-step reaction with 2 steps 1: potassium carbonate / butanone / 48 h / Reflux 2: sodium hydroxide; water / methanol / 3 h / Reflux
	Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 10 h / 85 °C 2: potassium hydroxide / 5 h / 105 °C
	Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 10 h / 85 °C 2: potassium hydroxide / 5 h / 105 °C

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]
[2]Scichilone [Gazzetta Chimica Italiana, 1882, vol. 12, p. 452]
[3]Yao, Wenhuan; Gao, Yanzi; Yuan, Xiao; He, Baofeng; Yu, Haifeng; Zhang, Lanying; Shen, Zhihao; He, Wanli; Yang, Zhou; Yang, Huai; Yang, Dengke [Journal of Materials Chemistry C, 2016, vol. 4, # 7, p. 1425 - 1440]
[4]Chen, Cheng-Chih; Lin, Chih-Hung [Asian Journal of Chemistry, 2016, vol. 28, # 6, p. 1270 - 1274]
[5]Yao, Wenhuan; Gao, Yanzi; Li, Fasheng; Zhang, Lanying; Yang, Zhou; Yang, Huai [RSC Advances, 2016, vol. 6, # 90, p. 87502 - 87512]
[6]Yao, Wenhuan; Gao, Yanzi; Zhang, Cuihong; Li, Chenyue; Li, Fasheng; Yang, Zhou; Zhang, Lanying [Journal of Polymer Science, Part A: Polymer Chemistry, 2017, vol. 55, # 10, p. 1765 - 1772]

28
[ 120-47-8 ]
(+-)-2,3-epoxy-propionaldehyde diethylacetal [ No CAS ]
[ 115595-27-2 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 3027 - 3037

29
[ 120-47-8 ]
aqueous NaOH [ No CAS ]
[ 25458-44-0 ]

Reference： [1]Tetrahedron Asymmetry,1993,vol. 4,p. 687 - 694

30
[ 120-47-8 ]
aqueous NaOH [ No CAS ]
[ 78461-64-0 ]

Reference： [1]Synthetic Communications,1981,vol. 11,p. 167 - 178

31
[ 120-47-8 ]
aqueous NaOH [ No CAS ]
[ 1004-24-6 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2110 - 2114

32
[ 120-47-8 ]
aqueous NaOH [ No CAS ]
[ 145576-28-9 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2110 - 2114

33
[ 120-47-8 ]
[ 5438-19-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium ethylate; ethanol 2: ethanolic KOH-solution
	Multi-step reaction with 2 steps 1: sodium ethylate; ethanol 2: aq. NaOH solution
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide 2: sodium hydroxide; ethanol

Reference： [1]Pierce; Salsbury; Fredericksen [Journal of the American Chemical Society, 1942, vol. 64, p. 1691,1692]
[2]Cavill; Gibson [Journal of the Society of Chemical Industry, 1947, vol. 66, p. 274]
[3]Gruzdev; Akopova; Frolova [Russian Journal of General Chemistry, 2013, vol. 83, # 4, p. 652 - 658][Zh. Obshch. Khim., 2013, vol. 83, # 4, p. 564 - 570,7]

34
[ 120-47-8 ]
[ 3336-41-2 ]

Reference： [1]Gazzetta Chimica Italiana,1899,vol. 29 I,p. 387,388

35
[ 120-47-8 ]
[ 13205-46-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium ethylate; ethanol 2: ethanolic KOH-solution
	Multi-step reaction with 2 steps 1: caesium carbonate; potassium iodide / tetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: water; lithium hydroxide monohydrate / methanol / 12 h / 40 °C / Inert atmosphere

Reference： [1]Pierce; Salsbury; Fredericksen [Journal of the American Chemical Society, 1942, vol. 64, p. 1691,1692]
[2]Current Patent Assignee: WUXI APPTEC CO., LTD. - US2021/300908, 2021, A1

36
[ 120-47-8 ]
[ 500-76-5 ]

Reference： [1]Journal of the Chemical Society,1942,p. 347,352

37
[ 120-47-8 ]
[ 6214-45-5 ]

Reference： [1]Archiv der Pharmazie,1961,vol. 294 /66,p. 538 - 549

38
[ 120-47-8 ]
[ 540-51-2 ]
[ 1711-24-6 ]

Yield	Reaction Conditions	Operation in experiment
		In accordance with Scheme 1 below, an acrylic compound having an oxetanyl group (acrylic compound 1) was synthesized using 3-ethyl-3-hydroxymethyloxetane (OXT-101, manufactured by Toagosei Co., Ltd.). The 1H-NMR spectrum of the acrylic compound 1 is shown in Fig. 1. "x" in the figures indicates the peak of the impurities.

Reference： [1]Patent: EP1405850,2004,A1 .Location in patent: Page 8; 13-14

39
[ 120-47-8 ]
[ 109384-19-2 ]
[ 1972-28-7 ]
[ 210962-44-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; In tetrahydrofuran; ethyl acetate;	Step 1 Synthesis of ethyl 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoate: 1.7 g (10.2 mmol) of ethyl 4-hydroxybenzoate, 1.76 g (9.3 mmol) of 1-t-butoxycarbonyl-4-hydroxypiperidine, obtained by t-butoxycarbonylating 4-hydroxypiperidine with di-t-butyl dicarbonate in an ordinary manner, and 2.44 g (9.3 mmol) of triphenylphosphine were dissolved in 40 ml of tetrahydrofuran. 1.62 g (9.3 mmol) of diethyl azodicarboxylate was added to the obtained solution at room temperature, and they were stirred overnight. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the crude product was obtained. It was purified by the silica gel column chromatography to obtain the title compound. Yield: 1.57 g (4.5 mmol) (44%) H-NMR (CDCl3) d δ 1.38 (3H, t), 1.50 (9H, s)1.70-1.80 (2H, m), 1.90-2.00 (2H, m), 3.30-3.41 (2H, m), 3.63-3.75 (2H, m), 4.35 (2H, q), 4.55 (1H, m), 6.90 (2H, d), 8.00 (2H, d)
	With triphenylphosphine; In tetrahydrofuran; ethyl acetate;	Step 1 Synthesis of ethyl 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoate: 1.76 g (9.3 mmol) of 1-t-butoxycarbonyl-4-hydroxypiperidine, obtained by t-butoxycarbonylating 4-hydroxypiperidine with di-t-butyl dicarbonate by an ordinary method, 1.7 g (10.2 mmol) of ethyl 4-hydroxybenzoate and 2.44 g (9.3 mmol) of triphenylphosphine were dissolved in 40 ml of tetrahydrofuran. 1.62 g (9.3 mmol) of diethyl azodicarboxylate was added to the solution at room temperature and the resultant mixture was stirred overnight. The reaction mixture was treated with ethyl acetate as the extractant in an ordinary manner to obtain a crude product, which was purified by the silica gel column chromatography to obtain the title compound. Yield: 1.57 g (4.5 mmol) (44 %) H-NMR (CDCl3) δ 1.38 (3H, t), 1.50 (9H, s), 1.70-1.80 (2H, m), 1.90-2.00 (2H, m), 3.30-3.41 (2H, m), 3.63-3.75 (2H, m), 4.35 (2H, q), 4.55 (1H, m), 6.90 (2H, d), 8.00 (2H, d).
	With triphenylphosphine; In tetrahydrofuran; ethyl acetate;	Step 1: Synthesis of ethyl 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoate: 1.76 g (93 mmol) of 1-t-butoxycarbonyl-4-hydroxypiperidine, obtained by t-butoxycarbonylating 4-hydroxypiperidine with di-t-butyl dicarbonate, 1.7 g (10.2 mmol) of ethyl 4-hydroxybenzoate and 2.44 g (9.3 mmol) of triphenylphosphine were dissolved in 40 ml of tetrahydrofuran. 1.62 g (9.3 mmol) of diethyl azodicarboxylate was added to the obtained solution, and they were stirred overnight. The reaction mixture was treated with ethyl acetate as the extraction solvent in an ordinary manner to obtain the crude product, which was purified by the silica gel column chromatography to obtain the title compound. Yield: 1.57 g (4.5 mmol) (44 %) H-NMR (CDCl3) δ 1.38 (3H, t), 1.50 (9H, s)1.70-1.80 (2H, m), 1.90-2.00 (2H, m), 3.30-3.41 (2H, m), 3.63-3.75 (2H, m), 4.35 (2H, q), 4.55 (1H, m), 6.90 (2H, d), 8.00 (2H, d)

With triphenylphosphine; In tetrahydrofuran;

Step 1 Synthesis of ethyl 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoate: 1.7 g (10.2 mmol) of ethyl 4-hydroxybenzoate, 1.76 g (9.3 mmol) of 1-t-butoxycarbonyl-4-hydroxypiperidine and 2.44 g (9.3 mmol) of triphenylphosphine were dissolved in 40 ml of tetrahydrofuran. 1.62 g (9.3 mmol) of diethyl azodicarboxylate was added to the solution at room temperature, and they were stirred overnight. The crude product was obtained by the same isolation process as that of step 1 in Example 1 with ethyl acetate as the extractant. After the purification by the silica gel column chromatography, the title compound was obtained. Yield: 1.57 g (4.5 mmol) (44%) H-NMR (CDCl3) δ 1.38 (3H, t), 1.50 (9H, s)1.70-1.80 (2H, m), 1.90-2.00 (2H, m), 3.30-3.41 (2H, m), 3.63-3.75 (2H, m), 4.35(2H, q), 4.55(1H, m),6.90 (2H, d), 8.00 (2H, d)

Reference： [1]Patent: US2001/56123,2001,A1
[2]Patent: EP976722,2000,A1
[3]Patent: EP1065200,2001,A1
[4]Patent: EP976722,2000,A1

40
[ 39238-07-8 ]
[ 120-47-8 ]
[ 263270-62-8 ]
[ 263270-64-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4-dichlorophenoxyacetic acid dimethylamine; potassium carbonate	30 N-{4-methyl-3-[4-(2-methylthiazol4-ylmethoxy)benzamido]phenyl}-2-morpholinopyridine-4-carboxamide The 4-(2-methylthiazol-4-ylmethoxy)benzoic acid used as a starting material was obtained as follows: A mixture of 4-chloromethyl-2-methylthiazole (13.3 g), ethyl 4-hydroxybenzoate (10 g), potassium carbonate (24.9 g) and DMA (200 ml) was stirred and heated to 80° C. for 18 hours. The mixture was cooled to ambient temperature and poured into water (1300 ml). The resultant precipitate was isolated and dried. There was thus obtained ethyl 4-(2-methylthiazol-4-ylmethoxy)benzoate (15.34 g); NMR Spectrum: (DMSOd6) 1.38 (t, 3H), 2.74 (s, 3H), 4.35 (m, 2H), 5.2 (s, 2H), 7.01 (d, 2H), 7.15 (s, 1H), 7.99 (d, 2H).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US6455520, 2002, B1

41
[ 120-47-8 ]
[ 115-11-7 ]
[ 13205-47-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; sulfuric acid; In ethanol; dichloromethane; water;	Reference Example 3 Synthesis of 4-tert-butoxybenzoic acid Ethyl 4-hydroxybenzoate (16.6 g), isobutene (25 g), and 95% sulfuric acid (0.5 ml) were stirred in dichloromethane (300 ml) overnight at 0 C. The reaction mixture was washed with 20% sodium carbonate aqueous solution, dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was dissolved in ethanol (32 ml) and the solution, with potassium hydroxide (7.5 g) and water (6 ml) added thereto, was refluxed with stirring for 2 hours. The reaction mixture was neutralized with hydrochloric acid and then extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The resulting solid was recrystallized from ethyl acetate to yield 9.3 g of the aimed compound.

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 10745 - 10748
Angew. Chem.,2013,vol. 125,p. 10945 - 10948,4
[2]Patent: US5912258,1999,A

42
[ 120-47-8 ]
[ 2695-48-9 ]
[ 110683-61-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium hydroxide; potassium carbonate; In ethanol;	4.(1) Synthesis of p-(7-octenyloxy)benzoic acid 9.4 g of 8-bromo-1-octene, 9.0 g of ethyl p-hydroxybenzoate, and 7.6 g of potassium carbonate were refluxed in ethanol for 10 hours. Thereto added was an aqueous solution containing 2.4 g of sodium hydroxide, and then reflux was further continued for 10 hours. After conclusion of the reaction, the reaction solution was diluted with water, and the pH of the solution was lowered to 2 by dropping hydrochloric acid. The generated precipitate was collected, washed sufficiently with water, and dried, to obtain 10.8 g of the objective ether compound. (Yield: 89 %)
89%	With sodium hydroxide; potassium carbonate; In ethanol;	15.(1) Synthesis of p-(7-octenyloxy)benzoic acid 9.4 g of 8-bromo-1-octene, 9.0 g of ethyl p-hydroxybenzoate, and 7.6 g of potassium carbonate were refluxed in ethanol for 10 hours. Added thereto was an aqueous solution containing 2.4 g of sodium hydroxide, and reflux was further continued for 10 hours. After conclusion of the reaction, the reaction solution was diluted with water, and the pH of the diluted solution was lowered to 2 by dropping hydrochloric acid thereto. The generated precipitate was collected, and was then washed with water sufficiently and dried, to obtain 10.8 g of the objective ether compound. (Yield: 89 %)
	With potassium hydroxide; potassium carbonate; In acetone;	(III) 4-(7-octeneoxy) benzoic acid <strong>[2695-48-9]8-Bromo-1-octene</strong> (23.9 g, 0.125 mole), ethyl 4-hydroxybenzoate (18.28 g, 0.11 mole) and 18-crown-6 (1.35 g, 0.0055 mole) are dissolved in 150 ml of acetone in a 500 ml round-bottomed flask. Potassium carbonate (45.6 g, 0.33 mole) is added to the flask and the resulting mixture is stirred and refluxed for 24 hr. The mixture is filtered to remove the salts and the filtrate is evaporated under reduced pressure to yield a light yellow oil. 200 ml of 2M KOH is added to the oil and the resulting mixture is stirred and refluxed for five hours. The resulting clear yellow solution is cooled to room temperature and acidified with HCl. The resulting white precipitate is filtered off, washed with water, recrystallized from 125 ml of ethanol and dried under vacuum. Yield, 23.4 g (86% based on ethyl 4-hydroxybenzoate).

Reference： [1]Patent: EP355772,1991,A3
[2]Patent: EP355772,1991,A3
[3]Patent: US5237076,1993,A

43
[ 5308-28-1 ]
[ 120-47-8 ]
[ 405-87-8 ]
[ 459-46-1 ]
1-[4-(4-fluorobenzyloxy)benzoyl]-4-isobutylpiperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		5 1-[4-(4-fluorobenzyloxy)benzoyl]-4-isobutylpiperazine EXAMPLE 5 1-[4-(4-fluorobenzyloxy)benzoyl]-4-isobutylpiperazine It was synthesised in the manner identical to Example 3. Namely, ethyl 4-hydroxybenzoate (2.50 g) was benzylated with 4-fluorobenzyl bromide (2.84 g) and then hydrolyzed. From thus obtained 3.57 g of 4-(4-fluorobenzyloxy) benzoic acid, 1.24 g was subjected to a condensation reaction with 1-isobutylpiperazine (0.71 g), thereby yielding 1.08 g of the aimed compound. mp 109.0°-110.2° C.; 1 H-NMR (CDCl3)δ: 7.41(2H, d, J=8.8 Hz), 7.38(2H, d, J=8.8Hz), 7.08(2H, t, J=8.8 Hz), 6.96(2H, d, J=8.8 Hz), 5.05(2H, s), 3.85-3.35(4H, m), 2.50-2.25(4H, m), 2.10(2H, d, J=7.3 Hz), 1.88-1.71(1H, m), 0.90(6H, d, J=6.8 Hz).

Reference： [1]Current Patent Assignee: SHISEIDO COMPANY LIMITED - US5756505, 1998, A

44
[ 120-47-8 ]
[ 127164-83-4 ]
[ 68641-49-6 ]
[ 127164-84-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In hexane; chloroform; water; ethyl acetate; acetonitrile;	EXAMPLE 4 Ethyl 4-(4,4-dimethyl-6-thiochromanoyloxy)benzoate A solution of 280 mg (1.26 mmol) of 4,4-dimethyl-6-carboxythiochroman and 252 mg (2.52 mmol) of triethylamine in 15 ml of chloroform was stirred at room temperature for 0.5 hours and then treated with 481 mg (1.26 mmol) of bis(2-oxo-3-oxazolidinyl)phosphinic chloride. The reaction mixture was stirred for 0.5h, treated with 209 mg (1.26 mmol) of ethyl 4-hydroxybenzoate and then stirred at room temperature for a further 12 hours. The reaction mixture was washed successively with dilute HCl and saturated sodium bicarbonate solutions The organic layer was concentrated in-vacuo and the resultant crude product purified by flash chromatography (silica; 10% ethyl acetate in hexane) followed by reversed-phase high pressure liquid chromatography (Whatman Partisil M20 10/50 ODS-2; 10% water in acetonitrile) to give the title compound as a colorless oil. PMR (CDCl3): delta1.38 (6H, s), 1.42 (3H, t, J~7.0 Hz), 1.98 (2H, m), 3.07 (2H, m), 4.39 (2H, q, J~7.0 Hz), 7.20 (1H, d, J~9.0 Hz), 7.28 (2H, d, J~8.1 Hz), 7.82 (1H, dd, J~9.0, 1.8 Hz), 8.12 (2H, d, J~8.1 Hz), 8.17 (1H, d, J~1.8 Hz).

Reference： [1]Patent: US4895868,1990,A

45
[ 6705-33-5 ]
[ 120-47-8 ]
[ 1972-28-7 ]
ethyl 4-(2-pyrazinylmethoxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7.5 parts (38.7%)	With triphenylphosphine; In tetrahydrofuran; di-isopropyl ether; water;	a) To a stirred and cooled (?5 C.) solution of 8.3 parts of <strong>[6705-33-5]2-pyrazinemethanol</strong>, 13.3 parts of ethyl 4-hydroxybenzoate and 20.2 parts of triphenylphosphine in 178 parts of tetrahydrofuran was added dropwise a solution of 13.93 parts of diethyl azodicarboxylate in 45 parts of tetrahydrofuran. Upon completion, the reaction mixture was stirred over weekend. After evaporation, the residue was taken up in water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was stirred in 2,2'-oxybispropane. The precipitate was filtered off and the filtrate was evaporated. The residue was crystallized from 2-propanol, yielding 7.5 parts (38.7%) of ethyl 4-(2-pyrazinylmethoxy)benzoate; mp. 76.1 C. (interm. 9).

Reference： [1]Patent: US5070090,1991,A

46
[ 120-47-8 ]
[ 96-32-2 ]
[ 19360-67-9 ]

Reference： [1]New Journal of Chemistry,2008,vol. 32,p. 878 - 890

47
[ 120-47-8 ]
gelatin [ No CAS ]
[ 3413-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	In water; glycerol;	EXAMPLE 4 Preparation of Soft Capsules of Butylphthalide Preparation of Gelatin Solution: 100 g of gelatin, 40 g of glycerin, 120 g of water and 200 mg of ethylparaben are used. The gelatin solution is prepared by the same protocol as in Example 1. Preparation of the oily liquid of butylphthalide:

Reference： [1]Patent: US2008/319056,2008,A1

48
[ 3047-32-3 ]
[ 120-47-8 ]
[ 477949-72-7 ]

Yield	Reaction Conditions	Operation in experiment
		In accordance with Scheme 1 below, an acrylic compound having an oxetanyl group (acrylic compound 1) was synthesized using 3-ethyl-3-hydroxymethyloxetane (OXT-101, manufactured by Toagosei Co., Ltd.). The 1H-NMR spectrum of the acrylic compound 1 is shown in Fig. 1. "x" in the figures indicates the peak of the impurities.

Reference： [1]Patent: EP1405850,2004,A1 .Location in patent: Page 8; 13-14

49
[ 120-47-8 ]
[ 94847-10-6 ]
[ 1151767-50-8 ]

Yield	Reaction Conditions	Operation in experiment
70.1%	With potassium carbonate; sodium iodide In acetone for 48h; Reflux; Inert atmosphere;

Reference： [1]Location in patent: experimental part Zheng, Youxuan; Cardinali, Francois; Armaroli, Nicola; Accorsi, Gianluca [European Journal of Inorganic Chemistry, 2008, # 12, p. 2075 - 2080]

50
[ 120-47-8 ]
[ 7189-69-7 ]
[ 1139705-24-0 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 1463 - 1466

51
[ 120-47-8 ]
[ 59142-68-6 ]
[ 1196474-68-6 ]

Yield	Reaction Conditions	Operation in experiment
98.8%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 17h; Inert atmosphere;	1.E8.1 Bromo-4-fluoro benzaldehyde 10 g (49.26 mmol) and Ethyl 4-hydroxybenzoate 8.19 (49.26 mmol) were mixed in a solution of DMF (50 mL). To this was added potassium carbonate 10.21 g (73.89 mmol). The reaction mixture was stirred at 100° C. (oil bath) for 17 hour under N2. Cooled to room temperature, mixture of EtOAc and water was added. Stirred for 30 min, concentrated via rotary evaporation to remove most of organic solvent. Filtered, washed with water, dried to get the target molecule, 17 g (98.8% yield) as white solid. 1H NMR (DMSO-d6, 300 MHz) δ ppm 10.13 (s, 1H), 8.03 (d, 2H, J=8.7 Hz) , 7.89 (d, 1H, J=8.7 Hz), 7.45 (m, 1H), 7.26 (d, 2H, J=8.7 Hz), 7.19 (m, 1H), 4.30 (q, 2H) and 1.30 (t, 3H).
	With caesium carbonate In N,N-dimethyl-formamide at 80℃;

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2010/256092, 2010, A1 Location in patent: Page/Page column 76-77
[2]Location in patent: scheme or table Xia, Yi; Cao, Kathy; Zhou, Yasheen; Alley; Rock, Fernando; Mohan, Manisha; Meewan, Maliwan; Baker, Stephen J.; Lux, Sarah; Ding, Charles Z.; Jia, Guofeng; Kully, Maureen; Plattner, Jacob J. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2533 - 2536]

52
[ 120-47-8 ]
[ 1191-16-8 ]
[ 6630-24-6 ]

Yield	Reaction Conditions	Operation in experiment
71%	With indium(III) triflate In dichloromethane at 25℃; for 24h;

Reference： [1]Vece, Vito; Ricci, Jeremy; Poulain-Martini, Sophie; Nava, Paola; Carissan, Yannick; Humbel, Stephane; Dunach, Elisabet [European Journal of Organic Chemistry, 2010, # 32, p. 6239 - 6248]

53
[ 108-97-4 ]
[ 105-53-3 ]
[ 120-47-8 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2010,vol. 53,p. 457 - 459

54
[ 120-47-8 ]
[ 82640-04-8 ]

Reference： [1]Patent: WO2011/47877,2011,A1

55
[ 120-47-8 ]
[ 195062-62-5 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 6913 - 6917
[2]Journal of the American Chemical Society,2015,vol. 137,p. 1593 - 1600

56
[ 120-47-8 ]
[ 94-13-3 ]
[ 94-26-8 ]
[ 94-18-8 ]
[ 4191-73-5 ]
[ 4247-02-3 ]
[ 108-24-7 ]
[ 99-76-3 ]
[ 27739-15-7 ]
[ 27801-52-1 ]
[ 27739-14-6 ]
[ 24262-66-6 ]
[ 13031-45-3 ]
[ 54835-09-5 ]
[ 27739-13-5 ]

Reference： [1]Analytical Chemistry,2010,vol. 82,p. 9384 - 9392

57
[ 120-47-8 ]
[ 6240-11-5 ]
[ 1335146-89-8 ]

Yield	Reaction Conditions	Operation in experiment
	With di-tert-butyl-diazodicarboxylate; In tetrahydrofuran; at 20℃;	Ethyl 4-hydroxybenzoate (83 mg) and 1-adamantaneethanol (90 mg) were combined in tetrahydrofuran (2 mL). Polymer-supported triphenylphosphine (250 mg of 3 mmol/g) and di-tert-butyl azodicarboxylate (173 mg) were added. The reaction was stirred at room temperature overnight. The resin was removed by filtration through celite. The filtrate was concentrated under vacuum, and the residue was triturated with 95/5 hexanes/ether to afford the title compound.

Reference： [1]Patent: US2011/237553,2011,A1 .Location in patent: Page/Page column 34; 35

58
[ 120-47-8 ]
[ 146137-78-2 ]
[ 1337915-50-0 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 8936 - 8939

59
[ 120-47-8 ]
[ 2014-83-7 ]
[ 149288-99-3 ]

Yield	Reaction Conditions	Operation in experiment
92.2%	With potassium carbonate; In acetone; for 24h;Reflux;	To a solution of ethyl 4-hydroxybenzoate 12 (5.81 g, 0.035 mol) and K2CO3 (9.6 g, 0.07 mol) in acetone (80 mL), 3 (6.86 g, 0.035 mol) was added. The suspension was stirred vigorously, and heated to reflux for 24 h. On cooling the reaction mixture down to room temperature, the suspension was concentrated and diluted with water (100 mL) and then extracted with AcOEt (2 × 100 mL). The organic layers was washed with 10% NaOH solution (100 mL), dried with Na2SO4 and then concentrated in vacuo to afford 13 as a white solid (10.52 g, 92.20%). Mp 84-85 C. 1H-NMR (300 MHz, CDCl3): delta 1.36-1.40 (t, J = 7.2 Hz, 3H, CH3), 4.32-4.39 (q, J = 7.2 Hz, 2H, CH2), 5.32 (s, 2H, CH2), 7.02-7.05 (d, J = 8.7 Hz, 2H, Ar), 7.23-7.28 (t, J = 7.2 Hz, 1H, Ar), 7.36-7.38 (d, J = 7.2 Hz, 2H, Ar), 8.02-8.04 (d, J = 8.7 Hz, 2H, Ar); EI-MS (m/z): 324 (M)+.
		A mixture of 4-hydroxybenzoic acid ethyl ester (3.00 g,18.1 mmol), KOH (1.52 g, 27.1 mmol) and 40 mL of acetonitrilewas heated to reflux for 0.5h. Alkyl bromide or benzylchloride derivative (21.6 mmol) was added drop-wise to themixture. The mixture was heated under reflux for 3 h afterthe completion of reaction, the mixture was poured into 100mL of water. Aqueous layer was extracted with dichloromethane(30 mL 3). The organic layer was separated, driedover anhydrous MgSO4 and then evaporated to obtain thecrude product.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 49,p. 164 - 171
[2]Letters in drug design and discovery,2014,vol. 11,p. 628 - 635

60
[ 120-47-8 ]
[ 102908-37-2 ]
[ 1373210-89-9 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2146 - 2149

61
[ 120-47-8 ]
[ 92420-89-8 ]
[ 1376574-24-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With boron trifluoride diethyl etherate; In dichloromethane; at -20 - 15℃; for 4h;Inert atmosphere; Molecular sieve;	Powdered 4 A molecular sieves (5.02 g) were added to a solution of ethyl 4-hydroxybenzoate 4a (0.91 g, 5.00 mmol) and methyl 2,3,4-tri-O-acetyl-1-O-trichloroacetylimidoyl-alpha-d-glucopyranuronate 8 (3.35 g, 7.00 mmol) in dry DCM (20 mL). The mixture was cooled to -20 C and BF3·Et2O (0.246 mL, 2.00 mmol) was added dropwise. The mixture was allowed to warm gradually to 15 C under continued stirring for 4 h. The reaction was quenched with triethylamine and the mixture was then filtered through a pad of Celite and concentrated. The residue was purified by column chromatography (Silica gel, Pet ether/EtOAc 3:1 to 2.5: 2) giving rise to the glucuronide conjugate as an off-white solid (2.20 g, 92%); Recrytallization from MeOH gave the product 9a as a white block solid; mp 107-109 C; -27.6 (c 1.0, CHCl3); numax (KBr disc, cm-1) 1755 (CO), 1710 (CO); deltaH (400 MHz, CDCl3) 8.01 (d, 2H, J 8.8 Hz, H-3 and H-5), 7.01 (d, 2H, J 8.8 Hz, H-4 and H-6), 5.38-5.28 (m, overlapping signals, 3H, Glu H-2, H-3, H-4), 5.25 (d, 1H, J 7.0 Hz, Glu H-1), 4.35 (q, 2H, J 7.3 Hz, CH2CH3), 4.24 (d, 1H, J 9.4 Hz, Glu H-5), 3.71 (s, 3H, OCH3), 2.06 (s, 6H, 2× OAc), 2.05 (s, 3H, OAc), 1.38 (t, 3H, J 7.1 Hz, CH2CH3); deltaC (100.6 MHz, CDCl3) 170.2, 169.5, 169.3, 166.9, 166.1, 160.1, 131.7, 125.8, 116.4, 98.5, 72.9, 71.9, 71.1, 69.1, 61.1, 53.2, 20.7, 20.8 (two overlapping), 14.5; m/z (ESI+) 505 [M+Na]+, HRESIMS+ 505.1328, C22H26NaO12 requires 505.1322.

Reference： [1]Tetrahedron,2012,vol. 68,p. 4194 - 4201

62
[ 120-47-8 ]
[ 153559-49-0 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 3504 - 3511

63
[ 120-47-8 ]
[ 83883-26-5 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 691 - 694
[2]Patent: KR2017/109833,2017,A
[3]Patent: JP6473537,2019,B1

64
[ 120-47-8 ]
[ 1885-46-7 ]
[ 773134-78-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium hydroxide; In water; acetonitrile; at 20℃; for 0.0333333h;	General procedure: Into a 20 mL vial was placed the phenol or thiophenols (0.5 mmol, 1.0 equiv), acetonitrile (1.0 mL) and 6M aqueous KOH (1.0 mL). The mixture was stirred rapidly at room temperature and HCF2OTf (210 μ, 1.5 mmol, 3.0 equiv) was added at once. Note: the reactions are exothermic. The mixture was stirred vigorously for 2 minutes. The reaction was diluted with FLO (8 mL) and extracted with ether (2 x 8 mL). The combined organic layers were dried over MgSC , concentrated, and purified by silica gel chromatography.; The reaction was performed according to the general procedure for the difluoromethylation of phenols on a 0.5 mmol scale. The product was purified by silica gel chromatography to give 2a as a clear oil (98 mg, 90% yield). XH NMR (500 MHz, CDC13) δ 8.06 (d, J= 8.7 Hz, 2H), 7.15 (d, J= 8.5 Hz, 2H), 6.59 (t, J= 73.2 Hz, 1H), 4.37 (q, J= 7.1 Hz, 2H), 1.39 (t, J= 7.1 Hz, 3H). ljC NMR (151 MHz, CDC13) δ 165.66 (s), 154.61 (t, J (s), 1 18.59 (s), 115.40 (t, J= 261.0 Hz), 61.13 (s), 14.29 (s). 19F NMR (376 MHz, CDC13) δ -84.25 (d, J= 73.2 Hz).

Reference： [1]Patent: WO2014/107380,2014,A1 .Location in patent: Paragraph 0078-0082

65
[ 120-47-8 ]
[ 90925-43-2 ]

Reference： [1]Patent: WO2014/144836,2014,A2
[2]European Journal of Medicinal Chemistry,2016,vol. 111,p. 138 - 159

66
[ 120-47-8 ]
[ 30432-16-7 ]
diethyl 4,4'-(2-(1,3-bis(4-(ethoxycarbonyl)phenoxy)propan-2-ylidene)propane-1,3-diyl)bis(oxy)dibenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium hydroxide; In ethanol; for 6h;Inert atmosphere; Schlenk technique; Reflux;	General procedure: Alkyl 4-hydroxy benzoate 2a,b (10 mmol) and potassium hydroxide (0.56 g, 10 mmol) were dissolved in absolute ethanol. 1,1,2,2-tetrayl-tetramethylene-tetrabromide (1) (1.00 g, 2.5 mmol) was then added into this solution. The reaction mixture was refluxed for 6 h. The mixture was cooled and filtrated. The white precipitate was filtered off and washed with H2O and crystallized from the appropriate solvent.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 139,p. 68 - 74

67
[ 120-47-8 ]
[ 13052-92-1 ]

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 462 - 475
[2]European Journal of Medicinal Chemistry,2016,vol. 120,p. 26 - 36

68
[ 2564-83-2 ]
[ 51934-41-9 ]
[ 73183-34-3 ]
[ 120-47-8 ]
[ 93-89-0 ]
[ 1609192-60-0 ]
[ 195062-62-5 ]

Reference： [1]Chemical Science,2016,vol. 7,p. 3676 - 3680

69
[ 13220-33-2 ]
[ 120-47-8 ]
ethyl 4-(1-methylpyrrolidin-3-yloxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 23℃; for 16h;Inert atmosphere;	A 100-mE round-bottom flask with a nitrogen ball was charged with piperidin-4-ol (1 g, 9.89 mmol), triphenylphosphine (3.5 g, 13.34 mmol), ethyl 4-hydroxybenzoate (2.25 g, 13.5 mmol), tetrahydroffiran (50 mE) and diethyl azodicarboxylate (3.45 g, 19.8 mmol). The resulting solution was stirred 16 h at 23° C. and concentrated under vacuum. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (1:1 v/v) to afford ethyl 4-(1 -methylpyrrolidin-3-yloxy)benzoate (0.5 g, 20percent). ECMS: (ESI) mlz 250 [M+H].

Reference： [1]Patent: US2016/185785,2016,A1 .Location in patent: Paragraph 2181; 2182

70
[ 120-47-8 ]
[ 105170-27-2 ]
ethyl 4-(5-methoxypyridin-2-yloxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With 2-Picolinic acid; potassium phosphate; copper(l) iodide; In dimethyl sulfoxide; at 90℃; for 16h;Inert atmosphere;	A 50-mE 3-necked round-bottom flask fitted with a nitrogen balloon, magnetic stir bar, condenser and thermometer was charged with ethyl 4-hydroxybenzoate (1.66 g, 9.99 mmol), DM50 (20 mE), Cul (95 mg, 0.50 mmol), picolinic acid (123 mg, 1.00 mmol), K3P04 (4.24 g, 19.97 mmol) and <strong>[105170-27-2]2-<strong>[105170-27-2]bromo-5-methoxypyridine</strong></strong> (1.88 g, 10.0 mmol). The resulting solution was stirred for 16 hat 90 C. After cooling to 25 C., the reaction was quenched with water (50 mE). The product was extracted with ethyl acetate (3x50 mE). The combined organic layers were washed with brine (50 mE), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography eluting with dichloromethane/methanol (10:1, v/v) to afford ethyl 4-(5-methoxypyridin-2-yloxy)benzoate as a yellow solid (1.20 g, 44%). ECMS: (ESI) mlz 274 [M+H].Step 1. Ethyl 4-(5-methoxypyridin-2-yloxy)benzoate

Reference： [1]Patent: US2016/185785,2016,A1 .Location in patent: Paragraph 2224; 2225

71
[ 120-47-8 ]
[ 142356-33-0 ]
ethyl 4-((6-((tert-butoxycarbonyl)umino)hexyl)oxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		A solution of compound 39 (3.00 g, 18.0 mmol) in DMF (80 mL) was charged with Cs2CO3 (11.7 g, 36.1 mmol) and stirred at room temperature for 5 mm. The above reaction mixture was charged with compound 40 (10.1 g, 36.1 mmol) and the reaction mixture was stirred at room temperature for 20 h. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (3 x 100 mL). The combined organic layers were concentrated and the residue purified by column chromatography to afford compound 41 (4.65 g, 70%) as a white gum which was directly used for next step; ESI MS m/z 366 [M + Hf.

Reference： [1]Patent: WO2016/123335,2016,A1 .Location in patent: Page/Page column 82; 83

72
[ 120-47-8 ]
[ 461-17-6 ]
ethyl 4-(4,4,4-trifluorobutoxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate; In butanone; for 4h;Reflux; Inert atmosphere;	Methyl ethyl ketone (5ml) solution of 4-hydroxybenzoate (0.46g, 2.80mmol), 1- iodo-4,4,4-trifluorobutane (0.67g, 2.80mmol) and anhydrous K2CO3 (1. 16g, a mixture of 8.40mmol), under an argon atmosphere, and heated under reflux for 4 hours. After cooling to room temperature, the solvent was removed under reduced pressure and the residue was partitioned between water (15ml) Et2O and (30 ml). The organic layer was separated, the aqueous phase was extracted with Et2O (2 × 20ml). The combined organic extracts were washed with brine (15ml), then dried (Na2SO4). The solvent was removed under reduced pressure to give a solid which was purified by flash chromatography (3: 1 hexanes / EtOAc) afford compound of the title with (0.67 g, 87%) as a colorless solid.

Reference： [1]Patent: JP5667058,2015,B2 .Location in patent: Paragraph 0489; 0490

73
[ 120-47-8 ]
[ 25458-44-0 ]

Reference： [1]Patent: JP2015/516972,2015,A
[2]Journal of Chemical Research,2020,vol. 44,p. 114 - 120

74
[ 120-47-8 ]
[ 6962-92-1 ]
C₁₅H₂₀O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl acetamide; at 100℃;	84.5 g of ethyl 4-hydroxybenzoate, 84.2 g of <strong>[6962-92-1]4-chlorobutyl acetate</strong>, 105 g of potassium carbonate and 254 g of N, N-dimethylacetamide were mixed, and the resulting mixture was heated to 100C and stirred. After cooling, methyl isobutyl ketone was added to the reaction mixture, and the mixture was washed with water and then the solvent was removed to obtain 126 g of an oily substance containing the compound (i) as a main component. Yield: 88% (based on ethyl 4-hydroxybenzoate).

Reference： [1]Patent: KR101677764,2016,B1 .Location in patent: Paragraph 0200-0203

75
[ 120-47-8 ]
[ 568-72-9 ]
ethyl 4-((1,6,6-trimethyl-10,11-dioxo-6,7,8,9,10,11-hexahydrophenanthro[1,2-b]furan-9-yl)oxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In chlorobenzene at 120℃; for 36h; Sealed tube; regioselective reaction;	Typical experimental procedure for the catalyst-free Aromatic ethers reaction. General procedure: A 10 mL sealed tube was charged with Tan-IIA substrates (0.1 mmol), various phenol (0.17 mmol), and TEMPO (0.2 mmol). PhCl (1 mL) was added, and the resulting mixture was stirred at 120°C. The reaction was monitored by TLC until the starting material disappeared. Then the solvent was removed under vacuum, and the resulting residue was purified by chromatography on a silica gel column to furnish the desired compound 4 as red solids.

Reference： [1]Liang, Bing; Yu, Shujuan; Li, Jie; Wang, Fan; Liang, Gaolin; Zhang, Ao; Ding, Chunyong [Tetrahedron Letters, 2017, vol. 58, # 19, p. 1822 - 1825]

76
[ 120-47-8 ]
[ 7462-74-0 ]
C₁₃H₁₇NO₄ [ No CAS ]

Reference： [1]Organic Syntheses,2007,vol. 84,p. 325 - 333

77
[ 120-47-8 ]
[ 87-66-1 ]
[ 31127-54-5 ]

Yield	Reaction Conditions	Operation in experiment
73.20%	With aluminum (III) chloride; In i-Amyl alcohol; at 90 - 130℃; for 4.5h;Inert atmosphere;	0.11mol of ethyl p-hydroxybenzoate, 0.1mol of pyrogallic acid, 0.013mol of aluminum trichlorideAnd isoamyl alcohol 450ml mixed in the reactor, the introduction of inert gas, when the system temperature was raised to 90-100 , stop the access,Continue to heat the reaction at 110-130 4.5h, TLC trace to the end of the reaction, the reaction temperature was cooled to 50-60 , incubated 1.5h,Water 150ml was added and the layers were separated. The organic layer was crystallized at 0-5 C, filtered and dried to give the product. The molar yield of the product was 73.20%HPLC ? 98.5%.
70.8%	With sulfuric acid; at 50 - 130℃; under 750.075 - 37503.8 Torr; for 3.5h;Inert atmosphere;	The acylating agent was 0.11 mol of ethyl p-hydroxybenzoate and 0.1 mol of pyrogallic acid,Concentrated sulfuric acid 0.015 mol was mixed in a reactor,Into the inert gas 30min,When the system temperature rose to 70-80 ,Closed reactorAt 110-130 ,Pressure 0.1-5MPa,Closed reaction 2h,The reaction was cooled to 50-60 C,Insulation 1h,Add 20% ethanol 300ml,Crystallization at 0-5 ,Filter drying,To get the product.The molar yield of the product was 70.80%HPLC ? 98.5%.

Reference： [1]Patent: CN106365961,2017,A .Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046; 0047
[2]Patent: CN106349036,2017,A .Location in patent: Paragraph 0044-0049

78
[ 120-47-8 ]
[ 84449-80-9 ]

Reference： [1]Patent: WO2018/144900,2018,A1

79
[ 120-47-8 ]
[ 41014-43-1 ]
ethyl 4-(benzo[d]oxazol-2-ylmethoxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67.34%	With potassium carbonate; In acetone; for 4h;Reflux;	General procedure: To a solution of various substituted phenols (1 mmol) in dry acetone (30 mL) K2CO3 (1 mmol)and compound 3 or 4 (1 mmol) were added. After being stirred for 4 h at reflux temperature, thereaction mixture was cooled, filtered, and concentrated under vacuum. Then the residue was dilutedwith 30 mL ethyl acetate and sequentially washed with 30 mL 1 M HCl, aq. NaHCO3 solution andbrine in order. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification of theresidue by chromatography on silica gel furnished target compounds. 1H-NMR, 13C-NMR and massspectroscopy (MS) of compounds 5a-m and 6a-m are shown in Supplementary Materials.

Reference： [1]Molecules,2018,vol. 23

80
[ 120-47-8 ]
[ 37859-43-1 ]
ethyl 4-(benzo[d]thiazol-2-ylmethoxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36.42%	With potassium carbonate; In acetone; for 4h;Reflux;	General procedure: To a solution of various substituted phenols (1 mmol) in dry acetone (30 mL) K2CO3 (1 mmol)and compound 3 or 4 (1 mmol) were added. After being stirred for 4 h at reflux temperature, thereaction mixture was cooled, filtered, and concentrated under vacuum. Then the residue was dilutedwith 30 mL ethyl acetate and sequentially washed with 30 mL 1 M HCl, aq. NaHCO3 solution andbrine in order. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification of theresidue by chromatography on silica gel furnished target compounds. 1H-NMR, 13C-NMR and massspectroscopy (MS) of compounds 5a-m and 6a-m are shown in Supplementary Materials.

Reference： [1]Molecules,2018,vol. 23

81
[ 120-47-8 ]
[ 437383-99-8 ]

Reference： [1]Archives of Pharmacal Research,2018,vol. 41,p. 1149 - 1161

82
[ 120-47-8 ]
[ 129623-61-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2018,p. 727 - 736

83
[ 120-47-8 ]
[ 54512-75-3 ]
ethyl 4-((5-chloropentyl)oxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; In acetone; for 10h;Reflux;	General procedure: To a solution of 4-hydroxybenzoate (1.00g, 6.02mmol, 1.0 eq) in acetone (25mL), 1-bromo-2-chloroethane (1.29g, 9.036mmol, 1.5 eq) and K2CO3 (2.49g, 3.0 eq) were added. The reaction was refluxed and stirred for 10h, then it was hot filtered and concentrated under vacuum. The obtained crude 20 was purified via flash column chromatography, mobile phase toluene to give 1.60g of neat compound as colorless oil, yield 86%.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 178,p. 243 - 258

84
[ 120-47-8 ]
[ 7250-67-1 ]
ethyl 4-[2-(pyrrolidin-1-yl)ethoxy]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2h;	To a stirred solution of ethyl 4-hydroxybenzoate (5.00 g, 30.1 mmol) in DMF (40 ml_) was added potassium carbonate (20.8 g, 150 mmol), and 1-(2-chloroethyl)pyrrolidine- hydrogen chloride (6.79 g, 98 % purity, 39.1 mmol) and the mixture was heated to 100C for 2 h. Water was added, and the mixture was extracted with ethyl acetate. The organic phase was dried (sodium sulfate), filtered and the solvent was removed in vacuum. Aminophase-silicagel chromatography gave 7.30 g (92 % yield) of the title compound. LC-MS (Method 2): Rt = 12.00 min; MS (ESIpos): m/z = 264 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 1 .281 (7.1 1 ), 1 .299 (16.00), 1 .317 (7.26), 1.657 (2.69), 1 .662 (2.28), 1 .665 (4.00), 1 .670 (3.48), 1 .674 (8.16), 1.683 (3.94), 1 .691 (2.79), 2.520 (2.81 ), 2.523 (2.88), 2.776 (3.21 ), 2.791 (7.02), 2.805 (3.36), 4.121 (3.33), 4.136 (6.89), 4.150 (3.18), 4.239 (2.07), 4.257 (6.57), 4.275 (6.46), 4.293 (1 .97), 7.030 (6.16), 7.035 (1 .85), 7.047 (1 .96), 7.052 (6.72), 7.882 (6.80), 7.887 (1.98), 7.899 (1 .95), 7.904 (6.66).

Reference： [1]Patent: WO2019/185525,2019,A1 .Location in patent: Page/Page column 69

85
[ 120-47-8 ]
[ 69610-40-8 ]
tert-butyl (2S)-2-[4-(ethoxycarbonyl)phenoxymethyl]pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 30℃; for 5h;	82.1 Step 1: Synthesis of tert-butyl (2S)-2-[4-(ethoxycarbonyl)phenoxymethyl]pyrrolidine-1-carboxylate To a stirred solution of tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (1 g, 4.97 mmol, 1.00 equiv) in THF (20 mL), ethyl 4-hydroxybenzoate (1.2 g, 7.22 mmol, 1.45 equiv), and PPh3 (2 g, 7.63 mmol, 1.53 equiv) were added at 0° C. This was followed by the addition of DEAD (1.2 mL) dropwise. The resulting solution was stirred for 5 h at room temperature. The reaction was then quenched by the addition of 20 mL of water. The resulting solution was diluted with 250 mL of EtOAc and washed with 50 mL of NH4Cl and 50 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with EtOAc/petroleum ether (1:4). This resulted in 1.5 g (86%) of the title compound as a solid. LCMS (ESI, m/z): 350.20 [M+H]+.

Reference： [1]Current Patent Assignee: RIBON THERAPEUTICS INC; RIBON THERAPEUTICS INC - US2019/330194, 2019, A1 Location in patent: Paragraph 1064

86
[ 120-47-8 ]
[ 23605-23-4 ]
N-(cyclohexyl)-[4-(ethoxycarbonyl)phenyloxy]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate In acetone for 12h; Reflux;	N-(cyclohexyl)-[4-(ethoxycarbonyl)phenyloxy]acetamide (16a) To a solution of ethyl 4-hydroxybenzoate (15, 118 mg, 0.71 mmol) in acetone (20 ml),was added, K2CO3 (1 g, 7.2 mmol) and N-cyclohexyl-2-chloroacetamide (1.23 mmol) and the mixture was stirred at reflux for 12h. The solvent was then evaporated to dryness and the crude mixture was extracted with a saturated aqueous K2CO3 and CH2Cl2. The organic layer was dried (Na2SO4) and vacuum-evaporated. The residue was purified by column chromatography (silica gel) using a mixture of cyclohexane/EtOAc 6/1 as the eluent, to provide compound 16a as white crystals. Yield: 81%.

Reference： [1]Lambrinidis, George; Gouedard, Cedric; Stasinopoulou, Sotiria; Angelopoulou, Angeliki; Ganou, Vassiliki; Meligova, Aggeliki K.; Mitsiou, Dimitra J.; Marakos, Panagiotis; Pouli, Nicole; Mikros, Emmanuel; Alexis, Michael N. [Bioorganic Chemistry, 2021, vol. 106]

87
[ 120-47-8 ]
[ 361-72-8 ]
ethyl 4-(3-amino-5-fluoro-2-nitrophenoxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.5 g	Stage #1: 2-amino-4,6-difluoronitrobenzene With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: Ethyl 4-hydroxybenzoate In tetrahydrofuran; mineral oil at 25℃; for 15.5h;	91.A A) Ethyl 4-(3-amino-5-fluoro-2-nitrophenoxy)benzoate To a solution of 3,5-difluoro-2-nitro-aniline (2.0 g) in THF (30 mL) was added 60% NaH (689 mg) at 0°C. After stirred for 30 min, ethyl 4- hydroxybenzoate (2.3 g) was added to the mixture. The mixture was stirred at 25°C for 15.5 h. The mixture was poured into Na2CO3 solution and extracted with EtOAc. The organic layer was washed with bine, dried with anhydrous Na2SO4, concentrated, and purified by silica gel column chromatography (petroleum ether/ethyl acetate = 50/1 to 9/1) to give the target compound (1.5 g) as a solid. 1H NMR (400 MHz, CDCl3) d: 8.03-8.13 (m, 2 H), 7.05-7.13 (m, 2 H), 6.29 (dd, J = 9.7, 2.6 Hz, 1 H), 6.03 (dd, J = 9.2, 2.6 Hz, 1 H), 5.52 (br s, 2 H), 4.31-4.44 (m, 2 H), 1.40 (t, J = 7.0 Hz, 3 H).

Reference： [1]Current Patent Assignee: STAMFORD ANDREW; POLVINO WILLIAM J - WO2021/26479, 2021, A1 Location in patent: Paragraph 00462-00463

88
[ 120-47-8 ]
[ 106-95-6 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Ethyl 4-hydroxybenzoate; allyl bromide With potassium carbonate In acetone for 24h; Reflux; Inert atmosphere; Stage #2: With sodium hydroxide In diethyl ether	1.1 Add ethyl 4-hydroxybenzoate (0.2mol, 33.2g (g)), 3-bromopropene (0.25mol, 30.3g), K2CO3 (0.3mol, 42.0g) and acetone to a 500ml (ml) glass reactor (300ml). After the inside of the reactor was sufficiently exchanged with nitrogen, the reactant was refluxed under a nitrogen flow for 24 hours. After adding diethyl ether (150 ml) and water (100 ml), the diethyl ether layer was washed 3 times with NaOH 10% solution (100 ml). The diethyl ether was evaporated, and a 2N HCl solution was added until the pH reached 2. The reaction product was washed with cold water and recrystallized with ethanol to prepare a compound represented by the following Chemical Formula 4-1-1.

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD. - CN112794829, 2021, A Location in patent: Paragraph 0191-0196

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 120-47-8 ] {[proInfo.proName]}

Quality Control of [ 120-47-8 ]

Related Doc. of [ 120-47-8 ]

Product Details of [ 120-47-8 ]

Calculated chemistry of [ 120-47-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 120-47-8 ]

Application In Synthesis of [ 120-47-8 ]

[ 120-47-8 ] Synthesis Path-Upstream 1~22

[ 120-47-8 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry