[ CAS No. 1700-37-4 ] {[proInfo.proName]}

Name: 1700-37-4|3-Benzyloxybenzaldehyde|98%
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SKU: A166057
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3d Animation Molecule Structure of 1700-37-4

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Quality Control of [ 1700-37-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1700-37-4 ]

Product Details of [ 1700-37-4 ]

CAS No. :	1700-37-4	MDL No. :	MFCD00003367
Formula :	C₁₄H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	CHOC₆H₄OCH₂C₆H₅	InChI Key :	JAICGBJIBWDEIZ-UHFFFAOYSA-N
M.W :	212.24	Pubchem ID :	74342
Synonyms :

Calculated chemistry of [ 1700-37-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	62.81
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.37
Log Po/w (XLOGP3) :	3.25
Log Po/w (WLOGP) :	2.93
Log Po/w (MLOGP) :	2.6
Log Po/w (SILICOS-IT) :	3.57
Consensus Log Po/w :	2.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.49
Solubility :	0.068 mg/ml ; 0.00032 mol/l
Class :	Soluble
Log S (Ali) :	-3.48
Solubility :	0.0709 mg/ml ; 0.000334 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.01
Solubility :	0.00205 mg/ml ; 0.00000966 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.66

Safety of [ 1700-37-4 ]

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 [ 1700-37-4 ]

* 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 [ 1700-37-4 ]
Downstream synthetic route of [ 1700-37-4 ]

[ 1700-37-4 ] Synthesis Path-Upstream 1~24

1
[ 1700-37-4 ]
[ 22483-09-6 ]
[ 7651-83-4 ]

Reference： [1] Chemical Communications, 2005, # 17, p. 2208 - 2210
[2] Journal of the American Chemical Society, 2011, vol. 133, # 32, p. 12451 - 12453

2
[ 1700-37-4 ]
[ 7651-83-4 ]

Reference： [1] Synthetic Communications, 1999, vol. 29, # 9, p. 1617 - 1625
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 25, p. 4983 - 4994

3
[ 100-39-0 ]
[ 100-83-4 ]
[ 1700-37-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14 h;	3-Hydroxybenzaldehyde (3 g, 24.6 mmol) and potassium carbonate (10.2 g, 73.8 mmol) were suspended in N,N-dimethylformamide (60 mL). Benzyl bromide (3.21 mL, 27.1 mmol) was added to this suspension, and stirred for 14 hours at room temperature. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1) to obtain the title compound (5.16 g, 99percent). ¹H-NMR Spectrum (CDCl₃) δ (ppm): 5.13 (2H, s), 7.24-7.25 (1H, m), 7.35-7.49 (8H, m), 9.98 (1H, s).
98%	With potassium carbonate In acetonitrile for 3 h; Reflux	[0284] In acetonitrile (50 mE) solvent, benzyl bromide (4.6 mE, 38.68 mmol) was added to a solution including 3-hy- droxybenzaldehyde (5.0 g, 40.94 mmol) and potassium carbonate (8.49 g, 61.43 mmol), and the reaction mixture was refluxed for 3 hours. After cooling, the reaction mixture was distributed between methylene chloride and watet An organic layer was dried by using Mg504 and filtered. The filtrate was evaporated, and water was added to the resultant solid. The solid was filtered and washed with water to obtain Compound 123a (8.53 g, 98percent).[0285] ‘H NMR (500 MHz, DMSO-d5) ö 9.97 (s, 1H),7.54-7.5 1 (m, 3H), 7.47 (d, 2H, J=7.5 Hz), 7.40 (t, 2H, J=7.0 Hz), 7.37-7.32 (m, 2H), 5.19 (s, 2H); ‘3C NMR (100 MHz, DMSO-d5) ö 193.6, 159.5, 138.3, 137.3, 131.1, 129.1, 128.6, 128.4, 123.4, 122.4, 114.6, 70.1.
98%	With potassium carbonate In acetonitrile for 3 h; Reflux	In acetonitrile (50 mL) solvent, benzyl bromide (4.6 mL, 38.68 mmol) was added to a solution including 3-hydroxybenzaldehyde (5.0 g, 40.94 mmol) and potassium carbonate (8.49 g, 61.43 mmol), and the reaction mixture was refluxed for 3 hours. After cooling, the reaction mixture was distributed between methylene chloride and water. An organic layer was dried by using MgSO4 and filtered. The filtrate was evaporated, and water was added to the resultant solid. The solid was filtered and washed with water to obtain Compound 123a (8.53 g, 98percent).

96%	With potassium carbonate In acetonitrile at 20℃;	[0043] In a 500 mL round-bottomed flask was added 3-hydroxybenzaldehyde (3.00 g, 24.57 mmol), potassium carbonate (6.80 g, 49.2 mmol), and benzyl bromide (2.92 mL, 24.57 mmol) in acetonitrile (150 mL) to give a brown suspension that was left stirring overnight at room temperature. The solvent was then evaporated, and the beige residue was diluted with water and extracted with ethyl acetate (3 x 75 mL). The organic layer was dried with magnesium sulfate and concentrated on a rotary evaporator. Purification by column chromatography (5percent ethyl acetate in hexanes) gave compound 1 as a white crystalline solid (5.0215 g, 23.66 mmol, 96percent). 1H NMR (400 MHz, CDC1₃) δ ppm 5.11 (s, 2 H) 7.32 - 7.52 (m, 9 H) 9.96 (s, 1 H). m/z 213 [M+H]⁺.
89%	With potassium carbonate In acetonitrile at 20℃; for 14 h;	To the solution of the 3-hydroxybenzaldehyde (1.43 g, 11.69 mmol) in acetonitrile were added benzyl bromide (2.0 g, 11.69 mmol) and potassium carbonate (3.23 g, 23.38 mmol) and stirred for 14 h at room temperature. After the completion of reaction, as indicated by TLC, solvent was removed in vacuo, the residue was diluted with water and extracted with ethyl acetate (3 × 20 mL). The separated organic layers were dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The residual oil was purified by flash chromatography (n-hexane/ethyl acetate 95:5) to yield compound 14 (2.2 g, 89percent) as white solid; R_f = 0.54 (n-hexane/ethyl acetate 95:5); ¹H NMR (400 MHz; CDCl₃; TMS) δ 9.97 (1H, s), 7.32–7.48 (8H, m), 7.23–7.26 (1H, m), 5.12 (2H, s).
81.1%	With potassium carbonate In ethanol	REFERENTIAL EXAMPLE 2 Production of N-methyl-3-benzyloxybenzylamine hydrochloride 15.0 g of m-hydroxybenzaldehyde was dissolved in 200 ml of ethanol, and 25.0 g of potassium carbonate and 32 g of benzyl bromide were added. With stirring, the mixture was heated under reflux for 6 hours. After the reaction, the insoluble inorganic salts were removed by filtration. The filtrate was evaporated under reduced pressure, and purified by silica gel column chromatography [Wakogel C-200, 150 g; hexane/chloroform=1/1] and then recrystallized from hexane to give 21.1 g (yield 81.1percent) of 3-benzyloxybenzaldehyde having a melting point of 56° to 57° C.
76%	With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere	A mixture of benzyl bromide (1.4 g; 8.2 mmol), 3-hydroxybenzaldehyde (1 .0 g; 8.2 mmol) and Cs₂CO₃ (2.67 g; 8.2 mmol) in anhydrous DMF (5 ml) was stirred overnight at room temperature under N₂. After evaporation of solvent in vacuo, the residue was diluted to 20 ml with CH₂CI₂ , washed with H₂O, brine, dried over anhydrous MgSO₄, filtered and filtrate evaporated to dryness to give the title compound (1 .33 g; 76percent) as creamy foam. ¹H-NMR (CDCI₃ ) 5.1 1 (s, 2H); 7.2 - 7.48 (m, 9H); 9.96 (s, 1 H)
8.59 g	With caesium carbonate In acetonitrile for 16 h; Reflux; Inert atmosphere	3-Hydroxybenzaldehyde (5.00 g, 0.041 mol) was dissolved in anhydrous acetonitrile (130 mL) under argon atmosphere. Cesium carbonate (20.01 g, 0.061 mol) was added and the suspension stirred for 5 min. Benzyl bromide (11.69 mL, 0.102 mol) was then added and the solution heated at reflux for 16 h. The solution was concentrated on rotary evaporator, water was added and the mixture was extracted with EtOAc. The organic phase was washed twice with water, once with brine, dried over MgSO₄, filtered and concentrated. Water was added and the mixture was extracted with CH₂Cl₂. The crude product was purified by flash chromatography on silica gel with hexanes/EtOAc (80/20) to yield 3a as a white solid (8.59 g). ¹H NMR δ (CDCl₃) 5.13 (s, 2H, PhCH₂O), 5.33 (s, 2H, COOCH₂Ph), 7.35-7.50 (m, 9H, 2-CH, 4-CH, 5-CH, 6-CH and PhCH₂O), 10.00 (s, 1H, PhCHO).

Reference： [1] Journal of the American Chemical Society, 1994, vol. 116, # 18, p. 8402 - 8403
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 7, p. 3188 - 3208
[3] Patent: US2007/105904, 2007, A1, . Location in patent: Page/Page column 112
[4] Molecules, 2010, vol. 15, # 11, p. 7971 - 7984
[5] Journal of the American Chemical Society, 2001, vol. 123, # 22, p. 5382 - 5383
[6] Patent: US2014/23603, 2014, A1, . Location in patent: Paragraph 0284; 0285
[7] Patent: KR101677122, 2016, B1, . Location in patent: Paragraph 0443-0444
[8] Journal of the American Chemical Society, 2010, vol. 132, # 40, p. 14021 - 14023
[9] Patent: WO2017/100757, 2017, A1, . Location in patent: Page/Page column 0043
[10] Journal of Medicinal Chemistry, 1991, vol. 34, # 7, p. 2176 - 2186
[11] Patent: WO2017/150903, 2017, A1, . Location in patent: Page/Page column 21
[12] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 3262 - 3271
[13] MedChemComm, 2017, vol. 8, # 2, p. 471 - 478
[14] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 12, p. 1599 - 1602
[15] Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 10, p. 2236 - 2238
[16] Patent: US5234946, 1993, A,
[17] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 7, p. 1621 - 1626
[18] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6384 - 6399
[19] Patent: WO2010/42998, 2010, A1, . Location in patent: Page/Page column 98
[20] Journal of Medicinal Chemistry, 1997, vol. 40, # 7, p. 1075 - 1089
[21] Farmaco, 2003, vol. 57, # 11, p. 909 - 916
[22] Journal of Fluorine Chemistry, 2003, vol. 119, # 2, p. 141 - 149
[23] Archiv der Pharmazie, 2017, vol. 350, # 5,
[24] Phytochemistry (Elsevier), 1982, vol. 21, # 11, p. 2663 - 2668
[25] Journal of Medicinal Chemistry, 1998, vol. 41, # 15, p. 2745 - 2753
[26] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 16, p. 2205 - 2208
[27] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 7, p. 1013 - 1015
[28] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 47 - 50
[29] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 5, p. 2697 - 2706
[30] Patent: WO2005/66194, 2005, A1, . Location in patent: Page/Page column 196-197
[31] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 6004 - 6008
[32] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4227 - 4237
[33] Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol. 26, # 5, p. 643 - 648
[34] Patent: US2014/37564, 2014, A1, . Location in patent: Paragraph 0314-0315
[35] Chemistry - An Asian Journal, 2015, vol. 10, # 4, p. 925 - 937
[36] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 14, p. 3218 - 3230
[37] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 1193 - 1199
[38] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3145 - 3157

4
[ 1700-30-7 ]
[ 1700-37-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 1,4-dioxane at 80℃; Schlenk technique	General procedure: In an oven dried Schlenk tube, were added alcohol 1 (69.0–199.5 mg, 0.5 mmol), CuI (10 molpercent)and 1,10-Phenanthroline (20 molpercent) and K3PO4 (2 mmol) followed by the addition of dioxane (2mL) at room temperature under open air atmosphere. The stirred reaction mixture was heated inan oil bath at 80 C for 7–48 h. Progress of the reaction was monitored by TLC till the reaction iscompleted. Then, the reaction mixture was cooled to room temperature, quenched with aqueousNH4Cl solution and then extracted with CH2Cl2 (3 10 mL). The organic layer was washed withsaturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent under reducedpressure and purification of the crude material by silica gel column chromatography (petroleumether/ethyl acetate) furnished the aldehyde/ketone 2 (61–97percent).

Reference： [1] Archiv der Pharmazie, 2007, vol. 340, # 5, p. 244 - 250
[2] Tetrahedron, 2006, vol. 62, # 14, p. 3389 - 3394
[3] Synthetic Communications, 2014, vol. 44, # 14, p. 2076 - 2087
[4] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 14, p. 1791 - 1793

5
[ 100-44-7 ]
[ 100-83-4 ]
[ 1700-37-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate In ethanol for 6 h; Reflux	A mixture of 3-hydroxybenzaldehyde (3 g, 24.59 mmol), benzyl chloride (4.1 mL, 35.79 mmol) and anhydrous K₂CO₃ (2.4 g, 17.39 mmol) in absolute EtOH (30 mL) was refluxed for 6 h. Then the reaction mixture was concentrated to dryness, redissolved in 10 mL of CH₂Cl₂ and washed with 5percent aqueous NaOH (3 × 10 mL). The organic layer was dried with anhydrous Na₂SO₄ and evaporated to dryness. The residue was purified by silica gel column chromatography (hexane/EtOAc, 8:2) to afford 5.1 g of 3-benzyloxy-benzaldehyde (98percent) as a white solid. Mp: 54–56 °C; ¹H NMR (300 MHz, CDCl₃): δ = 9.85 (s, 1H, CHO), 7.32 (m, 9H, H-2, H-4, H-5, H-6, Ph), 5.11 (s, 2H, OCH₂Ph); ¹³C NMR (75 MHz, CDCl₃) δ 192.5 (CHO), 159.7 (C-3), 138.2 (C-1), 136.7 (C-1′), 130.5 (CH-5), 129.1 (CH-3′, CH-5′), 128.6 (CH-4′), 127.9 (CH-2′, CH-6′), 124.1 (CH-6), 122.6 (CH-4), 113.6 (CH-2), 70.6 (OCH₂Ph); ESMS m/z (percent): 213 (100) [M+1]⁺.
84%	With sodium carbonate In acetone	Step 1 Preparation of 3-Benzyloxybenzaldehyde 24.2 g (0.2 mol) of 3-hydroxybenzaldehyde and 25.32 g (0.2 mol) of benzyl chloride were placed in 500 ml of acetone and 21.2 g (0.2 mol) of sodium carbonate was added thereto. The resulting solution was stirred for 12 to 24 hours with heating, cooled to room temperature. The solvent was removed under a reduced pressure and the residue thus obtained was washed with water and the extracted with ethyl acetate twice. The organic layer was dried and the solvent was removed under a reduced pressure to obtain a residue. The residue was subjected to column chromatography using a mixture of n-hexane and ethyl acetate (9:1) as an eluent to obtain 35.6 g (yield 84percent) of the title compound as a colorless liquid. ¹H-NMR (CDCl₃, TMS) δ (ppm) 10.01 (s, 1H), 7.67-7.18 (m, 9H), 5.14 (s, 2H); MS (m/e): 212 (MW, 32), 121 (73), 91 (100).
79%	With potassium carbonate; potassium iodide In ethanol for 4.5 h; Reflux	A suspension of 3-hydroxy benzaldehyde 11, benzyl chloride 12, K₂CO₃ and KI in 50mL of EtOH was refluxed for 4.5h. After cooling the solid thus obtained was filtered and washed several times with H₂O. The crude product was purified by column chromatography. Yield, 79percent; dull white solid; m. p. 77–78°C; Rf=0.61.

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 22, p. 6589 - 6597,9
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 15, p. 1971 - 1974
[3] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 5, p. 1537 - 1544
[4] Tetrahedron, 1992, vol. 48, # 35, p. 7185 - 7196
[5] Tetrahedron, 1992, vol. 48, # 5, p. 819 - 830
[6] Patent: US6552080, 2003, B1,
[7] Angewandte Chemie - International Edition, 2018, vol. 57, # 19, p. 5325 - 5329[8] Angew. Chem., 2018, vol. 130, # 19, p. 5423 - 5427,5
[9] European Journal of Medicinal Chemistry, 2017, vol. 133, p. 365 - 378
[10] Journal of the Chemical Society, 1957, p. 513
[11] Journal of Biological Chemistry, 1957, vol. 225, p. 269,275
[12] Journal of the Chemical Society, 1935, p. 1533,1543
[13] Journal of the Chemical Society, 1965, p. 3645 - 3660
[14] Heterocycles, 1988, vol. 27, # 9, p. 2185 - 2196
[15] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 8, p. 941 - 944
[16] Farmaco, 2003, vol. 57, # 11, p. 909 - 916
[17] Journal of Medicinal Chemistry, 2002, vol. 45, # 23, p. 5058 - 5068
[18] Biochimie, 2013, vol. 95, # 4, p. 842 - 849
[19] European Journal of Medicinal Chemistry, 2013, vol. 68, p. 385 - 393

6
[ 100-39-0 ]
[ 591-31-1 ]
[ 1700-37-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 65℃; Inert atmosphere	A suspension of 3-hydroxybenzaldehyde (2.0 g, 16.4 mmol), K2CO3 (3.39 g, 24.6 mmol) and KI (0.07 g) in DMF (10 mL) was stirred and heated to 65 °C under nitrogen atmosphere. Benzyl bromide (2.53 mL, 21.3 mmol) was added dropwise. After the reaction mixture was stirred at 65 °C overnight, the mixture was cooled to room temperature. Water was added and the mixture was extracted with Et2O. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was triturated with cooled hexanes to give 3 (3.02 g, 87percent) as a white solid; mp 42–43 °C. 1H NMR (CDCl3): δ 9.97 (s, 1H), 7.48–7.43 (m, 5H), 7.41–7.38 (m, 2H), 7.35–7.32 (m, 1H), 7.26–7.24 (m, 1H), 5.12 (s, 2H).

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 2, p. 524 - 527

7
[ 100-39-0 ]
[ 99-06-9 ]
[ 1700-37-4 ]

Yield	Reaction Conditions	Operation in experiment
85.7%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3 h;	The 3 - hydroxybenzaldehyde (1.0 g, 8.2 mmol) dissolved in 15 ml DMF in, adding [...] (1.52 g, 9.0 mmol), potassium carbonate (1.35 g, 9.8 mmol), 80 °C reaction 3 hours, adding 15 ml distilled water, extracted with ethyl acetate twice (2 × 20 ml), then saturated sodium chloride solution for washing 1 time, dried with anhydrous sodium sulfate. Concentrated, column chromatography, eluting agent is petroleum ether: ethyl acetate=3:1, to obtain white solid 1.5 g, yield 85.7percent

Reference： [1] Patent: CN107151220, 2017, A, . Location in patent: Paragraph 0246; 0247; 0248; 0249; 0250

8
[ 22272-48-6 ]
[ 100-39-0 ]
[ 100-83-4 ]
[ 1700-37-4 ]

Reference： [1] Patent: US2003/8882, 2003, A1,

9
[ 100-83-4 ]
[ 100-51-6 ]
[ 1700-37-4 ]

Reference： [1] Organic Letters, 2004, vol. 6, # 3, p. 397 - 400

10
[ 93033-58-0 ]
[ 1700-37-4 ]

Reference： [1] Journal of the Indian Chemical Society, 2003, vol. 80, # 3, p. 184 - 186
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1876 - 1879

11
[ 100-39-0 ]
[ 1700-37-4 ]

Reference： [1] Patent: US6046212, 2000, A,

12
[ 19438-10-9 ]
[ 1700-37-4 ]

Reference： [1] Archiv der Pharmazie, 2007, vol. 340, # 5, p. 244 - 250

13
[ 79678-37-8 ]
[ 1700-37-4 ]

Reference： [1] Archiv der Pharmazie, 2007, vol. 340, # 5, p. 244 - 250

14
[ 99-06-9 ]
[ 1700-37-4 ]

Reference： [1] Archiv der Pharmazie, 2007, vol. 340, # 5, p. 244 - 250

15
[ 1700-37-4 ]
[ 2973-80-0 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1982, vol. 21, # 2, p. 95 - 97

16
[ 1700-37-4 ]
[ 3769-41-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 23, p. 7962 - 7966

17
[ 1700-37-4 ]
[ 587-33-7 ]

Reference： [1] Organic Process Research and Development, 2007, vol. 11, # 6, p. 1069 - 1075
[2] Organic Process Research and Development, 2007, vol. 11, # 6, p. 1069 - 1075

18
[ 1700-37-4 ]
[ 1700-31-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 8, p. 941 - 944
[2] Journal of Organic Chemistry, 1994, vol. 59, # 20, p. 5999 - 6007
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2950 - 2955
[4] Tetrahedron, 1992, vol. 48, # 5, p. 819 - 830
[5] Journal of the Chemical Society, 1965, p. 3645 - 3660
[6] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4227 - 4237

19
[ 141-82-2 ]
[ 1700-37-4 ]
[ 122024-75-3 ]

Reference： [1] Russian Journal of General Chemistry, 2005, vol. 75, # 7, p. 1113 - 1124

20
[ 141-82-2 ]
[ 1700-37-4 ]
[ 122024-75-3 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S433 - S435

21
[ 1700-37-4 ]
[ 85604-06-4 ]

Reference： [1] Journal of the American Chemical Society, 2010, vol. 132, # 40, p. 14021 - 14023
[2] Heterocycles, 2001, vol. 54, # 1, p. 259 - 274

22
[ 1700-37-4 ]
[ 91523-50-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 47 - 50
[2] Journal of Medicinal Chemistry, 1984, vol. 27, # 10, p. 1321 - 1325

23
[ 60-29-7 ]
[ 1700-37-4 ]
[ 104566-41-8 ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium borohydrid In ethanol; ammonia; water	REFERENTIAL EXAMPLE 1 Production of 3-benzyloxybenzylamine hydrochloride Three hundred milligrams of 3-benzyloxybenzaldehyde was dissolved in 15percent ammonia/ethanol, and the solution was stirred for 3 hours. Then, 100 mg of sodium borohydride was added, and the mixture was stirred for 1 hour. The reaction mixture was distilled under reduced pressure, and 20 ml of water and 20 ml of ethyl ether were added. The organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and the solvent was evaporated. The residue was recrystallized from a mixture of tetrahydrofuran and ethyl ether containing hydrogen chloride to give 140 mg (yield 40percent) of the captioned compound as colorless scales having a melting point of 155° to 159° C.

Reference： [1] Patent: US5234946, 1993, A,

24
[ 1700-37-4 ]
[ 593-56-6 ]
[ 104566-41-8 ]

Reference： [1] Patent: US5098900, 1992, A,

[ 1700-37-4 ] Synthesis Path-Downstream 1~53

1
[ 1700-37-4 ]
[ 88303-25-7 ]
[ 630-02-4 ]
[ 855748-60-6 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether

Reference： [1]Wasserman; Dawson [Journal of the American Chemical Society, 1949, vol. 71, p. 2588]

2
[ 1700-37-4 ]
[ 1700-30-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium tetrahydridoborate In methanol at 0 - 20℃; for 2h; Inert atmosphere;
98%	With sodium tetrahydridoborate In tetrahydrofuran at 23℃; for 4h;
87%	With sodium tetrahydridoborate In methanol at 0℃; for 0.5h;

	With lithium aluminium hydride; diethyl ether
	With sodium tetrahydridoborate
	With sodium tetrahydridoborate In ethanol; dichloromethane
	With sodium tetrahydridoborate In methanol; dichloromethane for 1h;
	With sodium tetrahydridoborate In isopropanol
	With sodium tetrahydridoborate In methanol at 20℃;
	With sodium tetrahydridoborate In methanol
	With lithium aluminium hydride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	4.1.2.1. 3-Benzyloxybenzyl bromide (3c) 3-Hydroxybenzaldehyde (5.00 g, 0.041 mol) was dissolved in anhydrous acetonitrile (130 mL) under argon atmosphere. Cesium carbonate (20.01 g, 0.061 mol) was added and the suspension stirred for 5 min. Benzyl bromide (11.69 mL, 0.102 mol) was then added and the solution heated at reflux for 16 h. The solution was concentrated on rotary evaporator, water was added and the mixture was extracted with EtOAc. The organic phase was washed twice with water, once with brine, dried over MgSO4, filtered and concentrated. Water was added and the mixture was extracted with CH2Cl2. The crude product was purified by flash chromatography on silica gel with hexanes/EtOAc (80/20) to yield 3a as a white solid (8.59 g). 1H NMR δ (CDCl3) 5.13 (s, 2H, PhCH2O), 5.33 (s, 2H, COOCH2Ph), 7.35-7.50 (m, 9H, 2-CH, 4-CH, 5-CH, 6-CH and PhCH2O), 10.00 (s, 1H, PhCHO). The aldehyde 3a was dissolved in anhydrous THF (200 mL) under argon and cooled to 0 °C. Lithium aluminum hydride (1.55 g, 0.041 mol) was added in small portions and the solution stirred at room temperature for 2 h. The reaction was then quenched using water (0.8 mL), a 10% wt aqueous NaOH solution (1.15 mL) and water again (1.9 mL) and left to settle. The suspension was then filtered and concentrated. Water was added and the mixture extracted with EtOAc, the organic phase dried over MgSO4, filtered and concentrated to yield 7.07 g crude alcohol 3b. 1H NMR δ (CDCl3) 4.68 (s, 2H, PhCH2OH), 5.08 (s, 2H, PhCH2O), 6.90-7.46 (m, 9H, 2-CH, 4-CH, 5-CH, 6-CH and PhCH2O).
	With sodium tetrahydridoborate In methanol at 0℃; Inert atmosphere;
	With sodium tetrahydridoborate; ethanol; calcium(II) chloride In tetrahydrofuran at 0 - 20℃;	The intermediate 33 (8.2 mmols) and calcium chloride (16.4 mmols) were dissolved in 55 mL of anhydrous ethanol and 27 mLs of THF. The solution was next cooled to 0° C. and sodium borohydride (16.4 mmols) was added slowly over several minutes to the reaction vessel. Upon warming to ambient temperature, the mixture was allowed to stir for an additional 15 hours. After this time, the flask was again cooled to 0° C. and the excess sodium borohydride was quenched with the addition of 5 mLs of 1N HCl. The aqueous layer was extracted with four 20 mL portions of EtOAc; the organic layers were then combined, washed with 10 mLs of brine and dried with MgSO4. After evaporation, the crude organic material was purified by flash chromatography and 6.7 mmols of the title product was recovered. 1H NMR (300 MHz, CDCl3) δ 7.49-7.24 (m, 5H), 7.06-6.88 (m, 2H), 5.08 (s, 21-1), 4.66 (s, 2H), 1.78 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 129.88, 128.83, 128.21, 127.72, 119.60, 114.35, 113.45, 70.17, 65.46.
	With lithium tetrahydridoborate; ethanol In tetrahydrofuran Cooling with ice;
	With methanol; sodium tetrahydridoborate for 1h; Cooling with ice;	5.1.3. Phenylmethanol (8a) General procedure: To a solution of compound 7a (1.06 g, 10 mmol) in methanol(10 mL) was added NaBH4 (0.57 g, 15 mmol). After stirring for 1 hwhile cooled with an ice-water bath, methanol was evaporatedand the residue was dissolved in EtOAc (100 mL). The organic layerwas washed with water (3 100 mL) and brine (3 100 mL), anddried over MgSO4 overnight. EtOAc was evaporated to give 8a ascolorless oil (2.01 g, yield: 94%). ESI-MS m/z 109.4 [M+H]+. The crude product was used directly in the next reaction without furtherpurification. Compounds 8b-8u, 8aa-8ff, 10v-10w, 17a-17b and 22a-22hwere prepared using the same procedure described above
	With sodium tetrahydridoborate In methanol at 0 - 20℃; for 2h;

Reference： [1]Nagasawa, Shota; Fujiki, Shogo; Sasano, Yusuke; Iwabuchi, Yoshiharu [Journal of Organic Chemistry, 2021, vol. 86, # 9, p. 6952 - 6968]
[2]Thakkar, Kshitij; Geahlen, Robert L.; Cushman, Mark [Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2950 - 2955]
[3]Sayama, Misa; Inoue, Asuka; Nakamura, Sho; Jung, Sejin; Ikubo, Masaya; Otani, Yuko; Uwamizu, Akiharu; Kishi, Takayuki; Makide, Kumiko; Aoki, Junken; Hirokawa, Takatsugu; Ohwada, Tomohiko [Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6384 - 6399]
[4]Oki; Iwamura [Bulletin of the Chemical Society of Japan, 1959, vol. 32, p. 955,958]
[5]Baxter,I. et al. [Journal of the Chemical Society, 1965, p. 3645 - 3660]
[6]Robin, Jean-Pierre; Landais, Yannick [Tetrahedron, 1992, vol. 48, # 5, p. 819 - 830]
[7]Van Oeveren; Jansen; Feringa [Journal of Organic Chemistry, 1994, vol. 59, # 20, p. 5999 - 6007]
[8]Yang, Li-Ming; Lin, Shwu-Jiuan; Yang, Tsang-Hsiung; Lee, Kuo-Hsiung [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 8, p. 941 - 944]
[9]Lisowski, Vincent; Enguehard, Cecile; Lancelot, Jean-Charles; Caignard, Daniel-Henri; Lambel, Stephanie; Leonce, Stephane; Pierre, Alain; Atassi, Ghanem; Renard, Pierre; Rault, Sylvain [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 16, p. 2205 - 2208]
[10]Renaudet, Olivier; Reymond, Jean-Louis [Organic Letters, 2004, vol. 6, # 3, p. 397 - 400]
[11]Location in patent: experimental part Fournier, Diane; Poirier, Donald [European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4227 - 4237]
[12]Fan, Yi Chiao; Kwon, Ohyun [Organic Letters, 2012, vol. 14, # 13, p. 3264 - 3267]
[13]Current Patent Assignee: UNIVERSITY OF VIRGINIA - US2012/214858, 2012, A1 Location in patent: Page/Page column 29
[14]Klöck, Cornelius; Herrera, Zachary; Albertelli, Megan; Khosla, Chaitan [Journal of Medicinal Chemistry, 2014, vol. 57, # 21, p. 9042 - 9064]
[15]Cao, Jiangying; Ma, Chunhua; Zang, Jie; Gao, Shuai; Gao, Qianwen; Kong, Xiujie; Yan, Yugang; Liang, Xuewu; Ding, Qin'ge; Zhao, Chunlong; Wang, Binghe; Xu, Wenfang; Zhang, Yingjie [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3145 - 3157]
[16]Wang, Hui; Yang, Ren-Yin; Xu, Bo [Chemistry - A European Journal, 2022, vol. 28, # 23]

3
[ 100-44-7 ]
[ 100-83-4 ]
[ 1700-37-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate In ethanol for 6h; Reflux;	A mixture of 3-hydroxybenzaldehyde (3 g, 24.59 mmol), benzyl chloride (4.1 mL, 35.79 mmol) and anhydrous K2CO3 (2.4 g, 17.39 mmol) in absolute EtOH (30 mL) was refluxed for 6 h. Then the reaction mixture was concentrated to dryness, redissolved in 10 mL of CH2Cl2 and washed with 5% aqueous NaOH (3 × 10 mL). The organic layer was dried with anhydrous Na2SO4 and evaporated to dryness. The residue was purified by silica gel column chromatography (hexane/EtOAc, 8:2) to afford 5.1 g of 3-benzyloxy-benzaldehyde (98%) as a white solid. Mp: 54-56 °C; 1H NMR (300 MHz, CDCl3): δ = 9.85 (s, 1H, CHO), 7.32 (m, 9H, H-2, H-4, H-5, H-6, Ph), 5.11 (s, 2H, OCH2Ph); 13C NMR (75 MHz, CDCl3) δ 192.5 (CHO), 159.7 (C-3), 138.2 (C-1), 136.7 (C-1′), 130.5 (CH-5), 129.1 (CH-3′, CH-5′), 128.6 (CH-4′), 127.9 (CH-2′, CH-6′), 124.1 (CH-6), 122.6 (CH-4), 113.6 (CH-2), 70.6 (OCH2Ph); ESMS m/z (%): 213 (100) [M+1]+.
92%	With potassium carbonate; potassium iodide In acetone for 6h; Heating;
92%	With potassium carbonate; potassium iodide In tetrahydrofuran for 6h; Heating;

88%	With potassium carbonate; sodium iodide In ethanol for 4h; Heating;
88%	In ethanol
84%	With anhydrous sodium carbonate In acetone	3.1 Step 1 Step 1 Preparation of 3-Benzyloxybenzaldehyde 24.2 g (0.2 mol) of 3-hydroxybenzaldehyde and 25.32 g (0.2 mol) of benzyl chloride were placed in 500 ml of acetone and 21.2 g (0.2 mol) of sodium carbonate was added thereto. The resulting solution was stirred for 12 to 24 hours with heating, cooled to room temperature. The solvent was removed under a reduced pressure and the residue thus obtained was washed with water and the extracted with ethyl acetate twice. The organic layer was dried and the solvent was removed under a reduced pressure to obtain a residue. The residue was subjected to column chromatography using a mixture of n-hexane and ethyl acetate (9:1) as an eluent to obtain 35.6 g (yield 84%) of the title compound as a colorless liquid. 1H-NMR (CDCl3, TMS) δ (ppm) 10.01 (s, 1H), 7.67-7.18 (m, 9H), 5.14 (s, 2H); MS (m/e): 212 (MW, 32), 121 (73), 91 (100).
80%	With potassium carbonate In N,N-dimethyl-formamide at 50 - 85℃; for 24h; Inert atmosphere;
79%	With potassium carbonate; potassium iodide In ethanol for 4.5h; Reflux;	4.1.1 Synthesis of 3-(benzyloxy)benzaldehyde (13) A suspension of 3-hydroxy benzaldehyde 11, benzyl chloride 12, K2CO3 and KI in 50mL of EtOH was refluxed for 4.5h. After cooling the solid thus obtained was filtered and washed several times with H2O. The crude product was purified by column chromatography. Yield, 79%; dull white solid; m. p. 77-78°C; Rf=0.61.
67%	With potassium carbonate In N,N-dimethyl-formamide for 1h; Reflux;	3-Benzyloxybenzaldehyde (1f) A mixture of 3-hydroxybenzalehyde (1e) (1.2 g, 9.8 mmol), benzyl chloride (1.5 g, 11.9 mmol), and potassium carbonate (2.0 g, 14.5 mmol) in N,N-dimethylformamide (DMF, 3 mL) was refluxed for 1 h. The reaction mixture was poured into water and acidified to pH 6 with 10% HCl. The solution was extracted with EtOAc, and the organic phase was concentrated and purified using Si gel CC (n-hexane-acetone, 15:1) to yield 3-benzyloxybenzaldehyde (1f) as a colourless crystal (1.4 g, 67% yield). 1H-NMR (CDCl3) H: 9.97 (1H, s, CHO), 7.33-7.49 (8H, m, H-4,5,6, OCH2C6H5), 7.25 (1H, m, H-2), 5.12 (2H, s, OCH2C6H5); 13C-NMR (CDCl3)C: 192.1 (CHO), 159.3 (C-3), 137.8 (C-1), 136.3 (C-1'), 130.1 (C-5), 128.7 (C-4'), 128.2 (C-3',5'), 127.6 (C-2',6'), 123.7 (C-6), 122.2 (C-4), 113.2 (C-2), 70.2 (OCH2C6H5); All other data are the same as reported (Lin et al. 2005).
36%	With potassium carbonate In ethanol for 6h; Reflux;
	With ethanol; potassium carbonate; sodium iodide
	With potassium carbonate; N,N-dimethyl-formamide at 100℃;
	With ethanol; potassium etoxide
	With sodium hydroxide
	With hydroxide In water monomer
	With potassium carbonate; sodium iodide In ethanol
	With potassium carbonate In ethanol Heating;
	With potassium carbonate In ethanol Heating;
	With potassium carbonate for 4h; Reflux;	Synthesis and structural characterization of oxadiazole derivatives General procedure: The compound 1 can be prepared by the reaction between vanillin and benzyl chloride. Briefly, a mixture of vanillin (1.52 g, 10 mmol) and benzyl chloride (1.39 g, 11 mmol) was added to a well-stirred ethanolic solution of K2CO3 and refluxed for 4 h. The mixture was then concentrated in vacuum. The residue was dissolved in CH3COOC2H5, filtered, and washed with 10% aqueous NaOH and saturated NaCl solution for three times. The organic layer was dried over MgSO4 and concentrated in vacuum.
	Stage #1: meta-hydroxybenzaldehyde With potassium carbonate In ethanol for 0.5h; Reflux; Stage #2: benzyl chloride In ethanol for 6h; Reflux;	General procedure: The hydroxyl group in aldehyde A was protected by etherizing with benzyl chloride before used in the following synthesis. Briefly, hydroxyl-substituted benzaldehyde (10mmol) and K2CO3 (2.07g, 15mmol) were refluxed in 10mL of 95% ethanol for 0.5h, then, benzyl chloride (1.55g, 12mmol) was added and refluxed for 6h. The reaction mixture was cooled to room temperature and filtered to remove inorganic salt. The organic solvent was removed under vacuum to yield benzoxyl-substituted benzaldehyde (>90%).
	With potassium carbonate In acetone for 4h; Reflux;	5.2. General procedure for the synthesis of 7-10 General procedure: Compound 6 was synthesized as previously reported [36].A mixture of hydroxyaromatic aldehydes (1.0 mmol), appropriatebenzyl chlorides (1.2 mmol), and anhydrous sodium carbonatewas stirred for 4 h in refluxing acetone. The solvent wasevaporated under reduced pressure and the residue was dissolvedin dichloromethane, washed using water and brine, dried overanhydrous MgSO4, and the solvent was removed under reducedpressure. The resulting residue was purified through silica gel columnchromatography (dichloromethane/PE, 5:1 v/v) to affordcompounds 2-5 as white solids. To a solution of each of compounds2-5 (1.0 mmol) and compound 6 (1.0 mmol) in absoluteethanol (5 mL), was added drops of glacial acetic acid and piperidine.The reaction mixture was stirred at 80° C for 2-6 h, until thecompletion of the reaction as evidenced through TLC. The resultingreaction mixture was concentrated to dryness, and purifiedthrough silica gel column chromatography (dichloromethane/methanol/acetic acid, 100:1:1) to afford the pure products 7-10.The yield, melting point and spectral data of each compound aregiven below.
	With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 3h;
	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;
	With potassium carbonate In N,N-dimethyl-formamide for 4h;	2.3. Synthesis of alkoxybenzaldehydes (22-25) General procedure: Hydroxybenzaldehyde 3b (4.1 mmol) at 0 °C was dissolved in DMF (8 mL). Then, potassium carbonate (6.1 mmol) was put in, and stirred for 15 min. After that, alkyl halide (8.2 mmol) was added at 0 °C and left on stirring for an hour. Then, reaction further stirred for 3 h. Afterwards, mixture was diluted with distilled water (50 mL), and extracted using EtOAc (50 mL ×3). Gradient column chromatography (eluent: n-hexanes 5% ethyl acetate: n-hexanes) was done to purify corresponding products (22-25) in 60-96% yields.

Reference： [1]Moreno, Laura; Parraga, Javier; Galan, Abraham; Cortes, Diego; Cabedo, Nuria; Primo, Jaime [Bioorganic and medicinal chemistry, 2012, vol. 20, # 22, p. 6589 - 6597,9]
[2]Chang, Chiung-Yun; Kuo, Sheng-Chu; Lin, Yi-Lee; Wang, Jih-Pyang; Huang, Li-Jiau [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 15, p. 1971 - 1974]
[3]Lin, Chin-Fen; Yang, Jai-Sing; Chang, Chiung-Yun; Kuo, Sheng-Chu; Lee, Miau-Rong; Huang, Li-Jiau [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 5, p. 1537 - 1544]
[4]Landais; Robin [Tetrahedron, 1992, vol. 48, # 35, p. 7185 - 7196]
[5]Robin, Jean-Pierre; Landais, Yannick [Tetrahedron, 1992, vol. 48, # 5, p. 819 - 830]
[6]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - US6552080, 2003, B1
[7]Argüelles, Alonso J.; Sun, Siyuan; Budaitis, Brenna G.; Nagorny, Pavel [Angewandte Chemie - International Edition, 2018, vol. 57, # 19, p. 5325 - 5329][Angew. Chem., 2018, vol. 130, # 19, p. 5423 - 5427,5]
[8]Manivannan, Elangovan; Amawi, Haneen; Hussein, Noor; Karthikeyan, Chandrabose; Fetcenko, Aubry; Narayana Moorthy, N.S. Hari; Trivedi, Piyush; Tiwari, Amit K. [European Journal of Medicinal Chemistry, 2017, vol. 133, p. 365 - 378]
[9]Abe, Naohito; Haba, Manami; Hara, Hirokazu; Kamiya, Tetsuro; Mizuno, Nagisa; Okubo, Satoshi; Oyama, Masayoshi; Yamaura, Takao [Natural Product Research, 2022]
[10]Kaczor, Aneta; Szemerédi, Nikoletta; Kucwaj-Brysz, Katarzyna; Dąbrowska, Monika; Starek, Małgorzata; Latacz, Gniewomir; Spengler, Gabriella; Handzlik, Jadwiga [ChemMedChem, 2021, vol. 16, # 15, p. 2386 - 2401]
[11]Bristow [Journal of the Chemical Society, 1957, p. 513]
[12]Armstrong; Shaw [Journal of Biological Chemistry, 1957, vol. 225, p. 269,275]
[13]Rapson; Robinson [Journal of the Chemical Society, 1935, p. 1533,1543]
[14]Baxter,I. et al. [Journal of the Chemical Society, 1965, p. 3645 - 3660]
[15]Bambagiotti-Alberti, Massimo; Coran, Silvia A.; Vincieri, Franco F.; Mulinacci, Nadia; Pieraccini, Giuseppe M.L. [Heterocycles, 1988, vol. 27, # 9, p. 2185 - 2196]
[16]Yang, Li-Ming; Lin, Shwu-Jiuan; Yang, Tsang-Hsiung; Lee, Kuo-Hsiung [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 8, p. 941 - 944]
[17]Kiec-Kononowicz; Szymanska [Il Farmaco, 2003, vol. 57, # 11, p. 909 - 916]
[18]Bermejo, Almudena; Andreu, Inmaculada; Suvire, Fernando; Léonce, Stephane; Caignard, Daniel H.; Renard, Pierre; Pierré, Alain; Enriz, Ricardo D.; Cortes, Diego; Cabedo, Nuria [Journal of Medicinal Chemistry, 2002, vol. 45, # 23, p. 5058 - 5068]
[19]Zhao, Chao; Liu, Zai-Qun [Biochimie, 2013, vol. 95, # 4, p. 842 - 849]
[20]Xi, Gao-Lei; Liu, Zai-Qun [European Journal of Medicinal Chemistry, 2013, vol. 68, p. 385 - 393]
[21]Liu, Hongyan; Sun, Danwen; Du, Hang; Zheng, Changji; Li, Jingya; Piao, Huri; Li, Jia; Sun, Liangpeng [European Journal of Medicinal Chemistry, 2019, vol. 172, p. 163 - 173]
[22]Liu, Wen-Shan; Wang, Rui-Rui; Yue, Hai; Zheng, Zhi-Hui; Lu, Xin-Hua; Wang, Shu-Qing; Dong, Wei-Li; Wang, Run-Ling [Journal of Biomolecular Structure and Dynamics, 2020, vol. 38, # 13, p. 3814 - 3824]
[23]Abdel-Mohsen, Heba T.; Abdullaziz, Mona A.; Ali, Mamdouh M.; El Diwani, Hoda I.; El Kerdawy, Ahmed M.; Flanagan, Keith J.; Mahmoud, Abeer E. E.; Ragab, Fatma A. F.; Senge, Mathias O. [Molecules, 2020, vol. 25, # 4]
[24]Umm-E-Farwa; Ullah, Saeed; Khan, Maria Aqeel; Zafar, Humaira; Atia-tul-Wahab; Younus, Munisaa; Choudhary, M. Iqbal; Basha, Fatima Z. [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 40]

4
[ 1700-37-4 ]
[ 1779-58-4 ]
[ 495399-41-2 ]

Reference： [1]Chemical and pharmaceutical bulletin,1994,vol. 42,p. 512 - 520

5
[ 1700-37-4 ]
[ 69026-14-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide; silver(l) oxide In water at 90℃; for 1h;
93%	With potassium permanganate In water; acetone for 10h; Ambient temperature;
79%	With dipyridinium dichromate In N,N-dimethyl-formamide for 48h; Ambient temperature;

With rat hepatic microsomal aldehyde dehydrogenase; NAD In phosphate buffer; N,N-dimethyl-formamide at 37℃;

Reference： [1]Tamagnan, Gilles; Gao, Yigong; Bakthavachalam, Venkatesalu; White, William L.; Neumeyer, John L. [Tetrahedron Letters, 1995, vol. 36, # 33, p. 5861 - 5864]
[2]Landais; Robin [Tetrahedron, 1992, vol. 48, # 35, p. 7185 - 7196]
[3]Hu, Hong; Mendoza, Jose S.; Lowden, Christopher T.; Ballas, Lawrence M.; Janzen, William P. [Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 9, p. 1873 - 1882]
[4]Martini, Robert; Murray, Michael [Chemical Research in Toxicology, 1996, vol. 9, # 1, p. 268 - 276]

6
[ 100-39-0 ]
[ 100-83-4 ]
[ 1700-37-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 12h;
100%	With potassium carbonate In N,N-dimethyl-formamide at 23℃; for 3h;
99%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14h;	61.1.1 3-Hydroxybenzaldehyde (3 g, 24.6 mmol) and potassium carbonate (10.2 g, 73.8 mmol) were suspended in N,N-dimethylformamide (60 mL). Benzyl bromide (3.21 mL, 27.1 mmol) was added to this suspension, and stirred for 14 hours at room temperature. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1) to obtain the title compound (5.16 g, 99%). 1H-NMR Spectrum (CDCl3) δ (ppm): 5.13 (2H, s), 7.24-7.25 (1H, m), 7.35-7.49 (8H, m), 9.98 (1H, s).

99%	With potassium carbonate In methanol; chloroform for 8h; Reflux;
98%	With potassium carbonate In methanol; chloroform Heating;
98%	With potassium carbonate In acetonitrile for 3h; Reflux;	11.1 1) Synthesis of 3-(benzyloxy)benzaldehyde(Compound 123a) [0284] In acetonitrile (50 mE) solvent, benzyl bromide (4.6 mE, 38.68 mmol) was added to a solution including 3-hy- droxybenzaldehyde (5.0 g, 40.94 mmol) and potassium carbonate (8.49 g, 61.43 mmol), and the reaction mixture was refluxed for 3 hours. After cooling, the reaction mixture was distributed between methylene chloride and watet An organic layer was dried by using Mg504 and filtered. The filtrate was evaporated, and water was added to the resultant solid. The solid was filtered and washed with water to obtain Compound 123a (8.53 g, 98%).[0285] ‘H NMR (500 MHz, DMSO-d5) ö 9.97 (s, 1H),7.54-7.5 1 (m, 3H), 7.47 (d, 2H, J=7.5 Hz), 7.40 (t, 2H, J=7.0 Hz), 7.37-7.32 (m, 2H), 5.19 (s, 2H); ‘3C NMR (100 MHz, DMSO-d5) ö 193.6, 159.5, 138.3, 137.3, 131.1, 129.1, 128.6, 128.4, 123.4, 122.4, 114.6, 70.1.
98%	With potassium carbonate In acetonitrile for 3h; Reflux;	1 Synthesis of 3-(benzyloxy)benzaldehyde In acetonitrile (50 mL) solvent, benzyl bromide (4.6 mL, 38.68 mmol) was added to a solution including 3-hydroxybenzaldehyde (5.0 g, 40.94 mmol) and potassium carbonate (8.49 g, 61.43 mmol), and the reaction mixture was refluxed for 3 hours. After cooling, the reaction mixture was distributed between methylene chloride and water. An organic layer was dried by using MgSO4 and filtered. The filtrate was evaporated, and water was added to the resultant solid. The solid was filtered and washed with water to obtain Compound 123a (8.53 g, 98%).
97%	Stage #1: meta-hydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 3.5h;
96%	With 18-crown-6 ether; potassium carbonate In propan-2-one Inert atmosphere;
96%	With potassium carbonate In acetonitrile at 20℃;	Synthesis of Compound 1 [0043] In a 500 mL round-bottomed flask was added 3-hydroxybenzaldehyde (3.00 g, 24.57 mmol), potassium carbonate (6.80 g, 49.2 mmol), and benzyl bromide (2.92 mL, 24.57 mmol) in acetonitrile (150 mL) to give a brown suspension that was left stirring overnight at room temperature. The solvent was then evaporated, and the beige residue was diluted with water and extracted with ethyl acetate (3 x 75 mL). The organic layer was dried with magnesium sulfate and concentrated on a rotary evaporator. Purification by column chromatography (5% ethyl acetate in hexanes) gave compound 1 as a white crystalline solid (5.0215 g, 23.66 mmol, 96%). 1H NMR (400 MHz, CDC13) δ ppm 5.11 (s, 2 H) 7.32 - 7.52 (m, 9 H) 9.96 (s, 1 H). m/z 213 [M+H]+.
96%	Stage #1: meta-hydroxybenzaldehyde With potassium carbonate In propan-2-one at 20℃; for 0.166667h; Stage #2: benzyl bromide In propan-2-one at 60℃; for 12h;	1.2.a Step a To a solution of 3-hydroxybenzaldehyde 7 (25 g, 204.85 mmol) in acetone (250 mL) was added potassium carbonate (42.46 g, 307.27 mmol). The suspension was stirred at room temperature for 10 min. Benzyl bromide (31.38 mL, 264.25 mmol) was added, and the resultant suspension was heated at 60 °C for 12 h. After cooling to room temperature, the suspension was filtered, the filter cake washed with acetone, and filtrate concentrated to a residue. The residue was purified by automated normal-phase chromatography and eluted with ethyl acetate/hexanes to give 3-(benzyloxy)benzaldehyde 8 as an off-white solid. (42 g, 96 % yield). 1H NMR (400 MHz, DMSO-d6) d ppm: 9.98 (s, 1H), 7.27-7.50 (m, 5H), 7.25-7.26 (m, 2H), 5.14 (s, 2H); GCMS: m/z 212.1 : (GCMS condition: column: HP-5 (30 m x 320 pm x 0.25 pm); gradient: 120 °C- 300 °C, 40 °C min-l; HPLC-UV analysis: retention time = 14.37 min; detection: 190-400 nm: peak area, 99.58 %; eluent A, 0.1 % TFA in water; eluent B, Acetonitrile; isocratic/gradient over 30 min with a flow rate of 1.0 mL min-l .
96%	Stage #1: meta-hydroxybenzaldehyde With potassium carbonate In propan-2-one at 20℃; for 0.166667h; Stage #2: benzyl bromide In propan-2-one at 60℃; for 12h;	1.a Step a. To a solution of 3-hydroxybenzaldehyde 7 (25 g, 204.85 mmol) in acetone (250 mL) was added potassium carbonate (42.46 g, 307.27 mmol). The suspension was stirred at room temperature for 10 min. Benzyl bromide (31.38 mL, 264.25 mmol) was added, and the resultant suspension was heated at 60 °C for 12 h. After cooling to room temperature, the suspension was filtered, the filter cake washed with acetone, and filtrate concentrated to a residue. The residue was purified by automated normal-phase chromatography and eluted with ethyl acetate/hexanes to give 3-(benzyloxy)benzaldehyde 8 as an off-white solid. (42 g, 96 % yield). 1H NMR (400 MHz, DMSO-d6) d ppm: 9.98 (s, 1H), 7.27-7.50 (m, 5H), 7.25-7.26 (m, 2H), 5.14 (s, 2H); GCMS: m/z 212.1 : (GCMS condition: column: HP-5 (30 m x 320 pm x 0.25 pm); gradient: 120 °C- 300 °C, 40 °C min-1 ; HPLC-UV analysis: retention time = 14.37 min; detection: 190-400 nm: peak area, 99.58 %; eluent A, 0.1 % TFA in water; eluent B, Acetonitrile; isocratic/gradient over 30 min with a flow rate of 1.0 mL min-1.
94%	Stage #1: meta-hydroxybenzaldehyde With N,N,N-trimethyl-2-hydroxyethyl-ammonium hydroxide In lithium hydroxide monohydrate at 20℃; for 0.25h; Stage #2: benzyl bromide In lithium hydroxide monohydrate at 20℃; for 24h;	the synthesis of O-substituted phenolic derivatives.[13] General procedure: A typical procedure: A flask was charged with phenol (3.0 mmol) and choline hydroxide (0.66 mL). Then, the mixture was stirred at room temperature in open air for 15 min. Next, benzyl bromide (3.0 mmol) was added into the flask, then the resulting mixture (two phases: top ChOH layer and bottom benzyl bromide layer) allowed to stir at room temperature for 24 h. The reaction mixture (two phases: top product layer and bottom aqueous ChOH layer) was extracted with diethyl ether (3 × 10 mL). The combined organic layers were washed with water, then dried with anhydrous Na2SO4, and evaporated under reduced pressure. The crude mixture was purified by column chromatography on silica gel (hexanes/ethyl acetate). Benzyl phenyl ether (3a); 1H NMR (400 MHz, CDCl3) δ (ppm): 7.48-7.40 (m, 4H), 7.37-7.28 (m, 3H), 7.03-6.97 (m, 3H), 5.10 (s, 2H); 13C NMR (100 MHz, CDCl3) δ (ppm): 158.8, 137.1, 129.5, 128.6, 127.9, 127.5, 120.9, 114.9, 69.9.
93%	With potassium carbonate In N,N-dimethyl-formamide for 18h; Ambient temperature;
90%	With potassium carbonate In acetonitrile Reflux;
89%	With potassium carbonate In acetonitrile at 20℃; for 14h;	12 5.1.12 3-Benzyloxybenzaldehyde (14) To the solution of the 3-hydroxybenzaldehyde (1.43 g, 11.69 mmol) in acetonitrile were added benzyl bromide (2.0 g, 11.69 mmol) and potassium carbonate (3.23 g, 23.38 mmol) and stirred for 14 h at room temperature. After the completion of reaction, as indicated by TLC, solvent was removed in vacuo, the residue was diluted with water and extracted with ethyl acetate (3 × 20 mL). The separated organic layers were dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The residual oil was purified by flash chromatography (n-hexane/ethyl acetate 95:5) to yield compound 14 (2.2 g, 89%) as white solid; Rf = 0.54 (n-hexane/ethyl acetate 95:5); 1H NMR (400 MHz; CDCl3; TMS) δ 9.97 (1H, s), 7.32-7.48 (8H, m), 7.23-7.26 (1H, m), 5.12 (2H, s).
89%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14h;
88%	With potassium carbonate In acetonitrile for 12h; Reflux;
85%	With N,N,N-tributyl-1-butanaminium iodide; sodium hydride In tetrahydrofuran
85%	With potassium carbonate In propan-2-one for 2h; Heating;
81.1%	With potassium carbonate In ethanol	R.2 Production of N-methyl-3-benzyloxybenzylamine hydrochloride REFERENTIAL EXAMPLE 2 Production of N-methyl-3-benzyloxybenzylamine hydrochloride 15.0 g of m-hydroxybenzaldehyde was dissolved in 200 ml of ethanol, and 25.0 g of potassium carbonate and 32 g of benzyl bromide were added. With stirring, the mixture was heated under reflux for 6 hours. After the reaction, the insoluble inorganic salts were removed by filtration. The filtrate was evaporated under reduced pressure, and purified by silica gel column chromatography [Wakogel C-200, 150 g; hexane/chloroform=1/1] and then recrystallized from hexane to give 21.1 g (yield 81.1%) of 3-benzyloxybenzaldehyde having a melting point of 56° to 57° C.
78%	With potassium carbonate In N,N-dimethyl-formamide for 7h; Ambient temperature;
78%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	4.1.35 3-(Benzyloxy)benzaldehyde (41) To a solution of 3-hydroxybenzaldehyde (10.0g, 81.89mmol, 1.0eq.) in DMF (60mL), K2CO3 (22.64g, 163.78mmol, 2.0eq.) and benzyl bromide (9.75mL, 81.89mmol, 1.0eq.) were added. After stirring the reaction mixture for 24h, 1M NaOH(aq) (20mL) and H2O (80mL) were added to the mixture, and extracted with Et2O (3×40mL). Combined ethereal phases were washed with H2O (2×50mL), saturated brine (40mL), dried over Na2SO4, filtered, and the volatiles were evaporatedin vacuo to furnish 41. Yield: 13.56g (78%) of white solid. mp=52.5-54.0°C.1H NMR (400MHz, CDCl3): δ 5.12 (s, 2H), 7.21-7.27 (m, 1H), 7.30-7.51 (m, 8H), 9.97 (s, 1H).
78%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	4.1.35 3-(Benzyloxy)benzaldehyde (41) To a solution of 3-hydroxybenzaldehyde (10.0g, 81.89mmol, 1.0eq.) in DMF (60mL), K2CO3 (22.64g, 163.78mmol, 2.0eq.) and benzyl bromide (9.75mL, 81.89mmol, 1.0eq.) were added. After stirring the reaction mixture for 24h, 1M NaOH(aq) (20mL) and H2O (80mL) were added to the mixture, and extracted with Et2O (3×40mL). Combined ethereal phases were washed with H2O (2×50mL), saturated brine (40mL), dried over Na2SO4, filtered, and the volatiles were evaporatedin vacuo to furnish 41. Yield: 13.56g (78%) of white solid. mp=52.5-54.0°C.1H NMR (400MHz, CDCl3): δ 5.12 (s, 2H), 7.21-7.27 (m, 1H), 7.30-7.51 (m, 8H), 9.97 (s, 1H).
77%	Stage #1: meta-hydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 8h;
76%	With Cs₂CO₃ In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	38.A A mixture of benzyl bromide (1.4 g; 8.2 mmol), 3-hydroxybenzaldehyde (1 .0 g; 8.2 mmol) and Cs2CO3 (2.67 g; 8.2 mmol) in anhydrous DMF (5 ml) was stirred overnight at room temperature under N2. After evaporation of solvent in vacuo, the residue was diluted to 20 ml with CH2CI2 , washed with H2O, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness to give the title compound (1 .33 g; 76%) as creamy foam. 1H-NMR (CDCI3 ) 5.1 1 (s, 2H); 7.2 - 7.48 (m, 9H); 9.96 (s, 1 H)
75%	With potassium carbonate In N,N-dimethyl-formamide at 90℃;
75%	With potassium carbonate In ethanol for 4h; Heating;
72%	With anhydrous sodium carbonate In ethanol for 12h; Heating;
71%	With potassium carbonate In propan-2-one Reflux; Inert atmosphere;
66%	Stage #1: meta-hydroxybenzaldehyde With potassium carbonate In propan-2-one at 0℃; for 0.0833333h; Stage #2: benzyl bromide In propan-2-one at 20℃; for 21h;	3-benzyloxybenzaldehyde 14 [45]. K2CO3 (4.9 g, 35.47 mmol, 2.0 equiv) was added to a solution of 3-hydroxybenzaldehyde (2.17 g, 17.74 mmol, 1.0 equiv) in acetone (89 mL) with at 0 °C. After 5 min, the benzyl bromide (3.34 g, 19.51 mmol, 1.1 equiv) was added in the mixture. The solution was stirred for 1 night at rt. After concentrating the mixture in vacuo, the crude was dissolved with EtOAc, then the organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude was purified by chromatography on silica gel column (CHX/EtOAc, gradient 100:0 to 90:10) and concentrated under reduced pressure to afford the compound 14 as a white powder (2.48 g, 66% isolated yield). M. p. 60 °C; 1 H NMR (CDCl3, 400 MHz, 295 K) δ 9.98 (s, 1H), 7.50-7.33 (m, 8H), 7.26 (m, 1H), 5.13 (s, 2H); 13C NMR (CDCl3, 100 MHz, 295 K) δ 192.2, 159.4, 137.9, 136.4, 130.2, 128.8 (2C), 128.3, 127.7 (2C), 123.8, 122.3, 113.3, 70.3.
47%	With potassium carbonate In propan-2-one for 5h; Reflux;
850 mg	With potassium carbonate In propan-2-one for 5h; Heating;
	With potassium-t-butoxide 1.) DMF, RT, 15 min, 2.) DMF, RT, 3 h; Yield given. Multistep reaction;
	With potassium carbonate In methanol Heating;
	In ethanol
	With potassium carbonate In N,N-dimethyl-formamide
	With potassium carbonate; potassium iodide In ethanol
	With Cs₂CO₃ In acetonitrile at 20℃; for 4h;	XX. 171 Benzaldehyde 171 [0334] In a 200 mL RB flask were added with 4g (32.8mmol) of 3- hydroxybenzaldehyde, 4. 3mL (36mmol) of benzylbromide and 12. 8g (39. 3mmol) of cesium carbonate in 40mL of acetonitrile. The reaction mixture was stirred for 4 h at room temperature before the solvent was removed under reduced pressure and the residue taken in 50 mL of ethyl acetate and washed successively with 20 mL saturated aqueous sodium bicarbonate, 20 mL 1N aqueous sodium hydroxide and 20mL brine, dried over magnesium sulfate, filtered and concentrated to give 171 in a quantitative yield, which was sufficiently pure to be used in the next step. 1H NMR (400MHz, CDCIs) 8 : 5.13 (s, 2H), 7.34-7. 50 (m, 9H), 9.96 (s, 1H).
	With potassium carbonate In N,N-dimethyl-formamide for 4h;
8.59 g	With Cs₂CO₃ In acetonitrile for 16h; Reflux; Inert atmosphere;	4.1.2.1. 3-Benzyloxybenzyl bromide (3c) 3-Hydroxybenzaldehyde (5.00 g, 0.041 mol) was dissolved in anhydrous acetonitrile (130 mL) under argon atmosphere. Cesium carbonate (20.01 g, 0.061 mol) was added and the suspension stirred for 5 min. Benzyl bromide (11.69 mL, 0.102 mol) was then added and the solution heated at reflux for 16 h. The solution was concentrated on rotary evaporator, water was added and the mixture was extracted with EtOAc. The organic phase was washed twice with water, once with brine, dried over MgSO4, filtered and concentrated. Water was added and the mixture was extracted with CH2Cl2. The crude product was purified by flash chromatography on silica gel with hexanes/EtOAc (80/20) to yield 3a as a white solid (8.59 g). 1H NMR δ (CDCl3) 5.13 (s, 2H, PhCH2O), 5.33 (s, 2H, COOCH2Ph), 7.35-7.50 (m, 9H, 2-CH, 4-CH, 5-CH, 6-CH and PhCH2O), 10.00 (s, 1H, PhCHO).
	With potassium carbonate In dimethyl sulfoxide at 20℃;
	With potassium carbonate In acetonitrile for 3h; Reflux;	11.2 2) Synthesis of 3-(benzyloxy)benzaldehyde (Compound 107b) In an acetonitrile (50 mL) solvent, benzyl bromide (4.6 mL, 38.68 mmol) was added to a solution including 3-hydroxybenzaldehyde (5.0 g, 40.94 mmol) and potassium carbonate (8.49 g, 61.43 mmol), and the reaction mixture was refluxed for 3 hours. After cooling, the reaction mixture was distributed between methylene chloride and water. An organic layer was dried by using MgSO4, and filtered. A filtrate was evaporated, and water was added to the resultant solid. The solid was filtered and washed with water to obtain Compound 107b. 1H NMR (500 MHz, DMSO-d6) δ 9.97 (s, 1H), 7.54-7.51 (m, 3H), 7.47 (d, 2H, J=7.5 Hz), 7.40 (t, 2H, J=7.0 Hz), 7.37-7.32 (m, 2H), 5.19 (s, 2H); 13C NMR (100 MHz, DMSO-d6) δ 193.6, 159.5, 138.3, 137.3, 131.1, 129.1, 128.6, 128.4, 123.4, 122.4, 114.6, 70.1.
	With potassium carbonate
	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;
	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;	General synthetic procedure to prepare the 3-benzyloxy-β-nitrostyrene analogues. General procedure: The 3-benzyloxy-β-nitrostyrene analogues (2a-k) were prepared via the synthesis of benzyloxybenzaldehydes followed by appropriately substituting the aromatic aldehydes with nitromethane (Scheme 1). The benzyloxybenzaldehyde derivatives (3a-k) were prepared according to a protocol described in the literature [33]. To a stirred solution of 3-hydroxybenzaldehyde (16.4mmol) in N,N-dimethylformamide (60mL), potassium carbonate (24.59mmol) was added in successive portions at room temperature. The appropriately substituted benzyl bromide (16.4mmol) was subsequently added and stirring continued for 48h. The reaction was quenched by pouring the reaction mixture into cold water (50mL). Compounds 3a-e and 3g resulted in a precipitate that was collected via filtration and washed with 100mL cold water. However, compounds 3f and 3h-k yielded an oily residue that was extracted with ethyl acetate, dried with magnesium sulphate and then the combined organic phase was evaporated to dryness. All the intermediates (3a-k) obtained were used without further purification in the next step. The 3-benzyloxy-β-nitrostyrene analogues (2a-k) examined in this study was prepared by the protocol described by Tanaka and co-workers [34]. Nitromethane (12.2mmol) and sodium methoxide (28% methanol solution, 9.8mmol) was added together and cooled to 0°C. In a separate round-bottom flask 9.4mmol of the appropriate benzyloxybenzaldehyde intermediate (3a-k) was mixed with methanol (20mL) and sodium methoxide (28% methanol solution, 1.48mmol). The latter mixture was added slowly to the first and stirring continued for 10minat room temperature. After the reaction mixture was cooled to 0°C, 5N aqueous hydrochloric acid solution (40mL) was added and the reaction mixture was stirred for 15minat room temperature. The resulting precipitate was collected via filtration to yield the crude 3-benzyloxy-β-nitrostyrene analogues. The desired 3-benzyloxy-β-nitrostyrene analogues (2a-k) were obtained after recrystallization from an appropriate solvent. The NMR results, of all the test compounds, indicated the exclusive formation of an E-isomer, as corroborated by a significant coupling constant (J) of approximately 13Hz.
	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h;	5.1.4. 2-(Benzyloxy)benzaldehyde (9v) General procedure: 2-Hydroxybenzaldehyde 7v (1.22 g, 10 mmol) and benzyl bromide(2.05 g, 12 mmol) were dissolved in DMF (20 mL). After additionof K2CO3 (2.07 g, 15 mmol), the mixture was heated at 80 Cfor 5 h. The reaction was quenched by addition of ice-cold water(100 mL). Then the mixture was extracted by EtOAc (3 100mL). The organic layer was washed by 10% HCl (3 100 mL), water(3 100 mL) and brine (3 100 mL), and dried over MgSO4 overnight.EtOAc was evaporated to give compound 9v as colorlessoil (1.80 g, yield: 85%). ESI-MS m/z 213.4 [M+H]+. The crude productwas used directly in the next reaction without furtherpurification.Compound 9w was prepared using the same proceduredescribed above.
	With potassium carbonate In dimethyl sulfoxide at 20℃;	General procedure: To a stirred solution of 4 (0.364 g, 2 mmol) and K2CO3 (0.552 g, 4 mmol) in DMSO (15 mL), and BnBr (0.44 mL, 4.4 mmol) was dropwise added at the room temperature. The reaction was then quenched by ice water, extracted with EtOAc (3 * 20 mL), then dried over Na2SO4, finally concentrated under reduced pressure to afford 5 (6.25 g). In the presence of 40% KOH, 5 reacted with corresponding benzaldehydes in a mixture of water and ethanol to obtain the chalcones 6a-g, which purified through a silica gel column. BCl3 (10 mL, 1 M in DCM) was dropwise added in anhydrous DCM (50 mL) of 6a-g (1.96 g, 10 mmol) under ice bath and stirring. After 0.5 h, the ice bath was removed, and the reaction was carried out for 2 h at room temperature. After being monitored by TLC, 15 mL ice water was added. The reaction was extracted with EtOAc (3 * 30 mL). The combined extract was dried over anhydrous Na2SO4 and was concentrated. The concentrated solution was purified by column chromatography to gain A1-7.
25 g	With potassium carbonate In Petroleum ether at 60℃; for 10h;	6.1 Step 1) Preparation of 3-(benzyloxy)benzaldehyde (201) Potassium carbonate (K2CO3, 112.5 g, 0.81 mol) and bromomethylbenzene (85 g, 0.50 mol) were added to asolution of 3-hydroxybenzaldehyde (50 g, 0.41 mol) in acetonitrile (ACN, 500 mL). The mixture was stirred at 60°C forabout 10 hours. After the reaction was completed, the reaction solution was filtered and then concentrated. Then,petroleum ether/ethyl acetate (PE/EA, 20: 1, 20 mL) was added thereto, and further stirred for about 1 hour, followedby concentration through a filter. Thereby, 3- (benzyloxy)benzaldehyde (201, 25 g) was obtained as a grayish whitesolid. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 9.97 (s, 1H), 7.54-7.51(m, 3H), 7.47 (d, J=7.2Hz, 2H), 7.42-7.34 (m, 4H),5.19 (s, 2H)
	Stage #1: meta-hydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 12h;

Reference： [1]Nicolaou; Bunnage; Bunnage, Mark E.; Koide; Koide, Kazunori [Journal of the American Chemical Society, 1994, vol. 116, # 18, p. 8402 - 8403]
[2]Nguyen, Trung Xuan; Abdelmalak, Monica; Marchand, Christophe; Agama, Keli; Pommier, Yves; Cushman, Mark [Journal of Medicinal Chemistry, 2015, vol. 58, # 7, p. 3188 - 3208]
[3]Current Patent Assignee: EISAI CO LTD - US2007/105904, 2007, A1 Location in patent: Page/Page column 112
[4]Location in patent: experimental part Choi, Taeyoung; Ma, Eunsook [Molecules, 2010, vol. 15, # 11, p. 7971 - 7984]
[5]Orner; Ernst; Hamilton [Journal of the American Chemical Society, 2001, vol. 123, # 22, p. 5382 - 5383]
[6]Current Patent Assignee: PUSAN NATIONAL UNIVERSITY - US2014/23603, 2014, A1 Location in patent: Paragraph 0284; 0285
[7]Current Patent Assignee: PUSAN NATIONAL UNIVERSITY - KR101677122, 2016, B1 Location in patent: Paragraph 0443-0444
[8]Gilmartin, Philip H.; Kozlowski, Marisa C. [Organic Letters, 2020, vol. 22, # 8, p. 2914 - 2919]
[9]Huang, Shenlin; Petersen, Tue B.; Lipshutz, Bruce H. [Journal of the American Chemical Society, 2010, vol. 132, # 40, p. 14021 - 14023]
[10]Current Patent Assignee: STATE UNIVERSITY SYSTEM OF FLORIDA - WO2017/100757, 2017, A1 Location in patent: Page/Page column 0043
[11]Current Patent Assignee: NESTLE S.A. - WO2019/228794, 2019, A1 Location in patent: Page/Page column 44; 45
[12]Current Patent Assignee: NESTLE S.A. - WO2020/229375, 2020, A1 Location in patent: Page/Page column 44
[13]Joo, Seong-Ryu; Kim, Seung-Hoi; Kwon, Gyu-Tae; Park, Soo-Youl [Bulletin of the Korean Chemical Society, 2020, vol. 41, # 12, p. 1200 - 1205]
[14]Bird; Bruneau; Crawley; Edwards; Foster; Girodeau; Kingston; McMillan [Journal of Medicinal Chemistry, 1991, vol. 34, # 7, p. 2176 - 2186]
[15]Current Patent Assignee: BIO-PHARM SOLUTIONS CO LTD - WO2017/150903, 2017, A1 Location in patent: Page/Page column 21
[16]Patel, Bhargav A.; Krishnan, Ramalingam; Khadtare, Nikhil; Gurukumar; Basu, Amartya; Arora, Payal; Bhatt, Aaditya; Patel, Maulik R.; Dana, Dibyendu; Kumar, Sanjai; Kaushik-Basu, Neerja; Talele, Tanaji T. [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 3262 - 3271]
[17]Chen, Hekai; Kong, Jun; Li, Tian; Xu, Qun; Yin, Hang; Zhang, Liwei [2021, vol. 12, # 10, p. 1771 - 1779]
[18]Lan, Jin-Shuai; Zhang, Tong; Liu, Yun; Zhang, Yong; Hou, Jian-wei; Xie, Sai-Sai; Yang, Jing; Ding, Yue; Cai, Zhen-zhen [MedChemComm, 2017, vol. 8, # 2, p. 471 - 478]
[19]Lee, Hee-Yoon; Sohn, Jeong-Hun; Kwon, Byoung-Mog [Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 12, p. 1599 - 1602]
[20]Venkateswarlu, Somepalli; Raju, Mudunuri S. S.; Subbaraju, Gottumukkala V. [Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 10, p. 2236 - 2238]
[21]Current Patent Assignee: MERCK & CO INC - US5234946, 1993, A
[22]Carvalho, Christopher F.; Sargent, Melvyn V. [Journal of the Chemical Society. Perkin transactions I, 1984, # 7, p. 1621 - 1626]
[23]Frlan, Rok; Gobec, Stanislav; Hrast, Martina; Knez, Damijan; Kos, Janko; Žakelj, Simon; Pišlar, Anja [Bioorganic Chemistry, 2022, vol. 119]
[24]Frlan, Rok; Gobec, Stanislav; Hrast, Martina; Knez, Damijan; Kos, Janko; Žakelj, Simon; Pišlar, Anja [Bioorganic Chemistry, 2022, vol. 119]
[25]Sayama, Misa; Inoue, Asuka; Nakamura, Sho; Jung, Sejin; Ikubo, Masaya; Otani, Yuko; Uwamizu, Akiharu; Kishi, Takayuki; Makide, Kumiko; Aoki, Junken; Hirokawa, Takatsugu; Ohwada, Tomohiko [Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6384 - 6399]
[26]Current Patent Assignee: AKAAL PHARMA - WO2010/42998, 2010, A1 Location in patent: Page/Page column 98
[27]Zwaagstra, Mariël E.; Timmerman, Hendrik; Tamura, Masahiro; Tohma, Tsutomu; Wada, Yasushi; Onogi, Kazuhiro; Zhang, Ming-Qiang [Journal of Medicinal Chemistry, 1997, vol. 40, # 7, p. 1075 - 1089]
[28]Kiec-Kononowicz; Szymanska [Il Farmaco, 2003, vol. 57, # 11, p. 909 - 916]
[29]Le Stang, Sylvie; Meier, Ralf; Rocaboy, Christian; Gladysz [Journal of Fluorine Chemistry, 2003, vol. 119, # 2, p. 141 - 149]
[30]Nagasawa, Shota; Fujiki, Shogo; Sasano, Yusuke; Iwabuchi, Yoshiharu [Journal of Organic Chemistry, 2021, vol. 86, # 9, p. 6952 - 6968]
[31]Toublet, François-Xavier; Lalut, Julien; Hatat, Bérénice; Lecoutey, Cédric; Davis, Audrey; Since, Marc; Corvaisier, Sophie; Freret, Thomas; Sopková-de Oliveira Santos, Jana; Claeysen, Sylvie; Boulouard, Michel; Dallemagne, Patrick; Rochais, Christophe [European Journal of Medicinal Chemistry, 2021, vol. 210]
[32]Krauss, Jürgen; Stadler, Martina; Bracher, Franz [Archiv der Pharmazie, 2017, vol. 350, # 5]
[33]Asakawa, Yoshinori; Campbell, Ella O. [Phytochemistry, 1982, vol. 21, # 11, p. 2663 - 2668]
[34]Astles, Peter C.; Brown, Thomas J.; Halley, Frank; Handscombe, Caroline M.; Harris, Neil V.; McCarthy, Clive; McLay, Iain M.; Lockey, Peter; Majid, Tahir; Porter, Barry; Roach, Alan G.; Smith, Christopher; Walsh, Roger [Journal of Medicinal Chemistry, 1998, vol. 41, # 15, p. 2745 - 2753]
[35]Lisowski, Vincent; Enguehard, Cecile; Lancelot, Jean-Charles; Caignard, Daniel-Henri; Lambel, Stephanie; Leonce, Stephane; Pierre, Alain; Atassi, Ghanem; Renard, Pierre; Rault, Sylvain [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 16, p. 2205 - 2208]
[36]Yang, Li-Ming; Lin, Shwu-Jiuan; Hsu, Fen-Lin; Yang, Tsang-Hsiung [Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 7, p. 1013 - 1015]
[37]Ma, Dawei; Wu, Wengen; Yang, Guoxin; Li, Jingya; Li, Jia; Ye, Qizhuang [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 47 - 50]
[38]Lin, Shwu-Jiuan; Tsai, Wei-Jern; Chiou, Wen-Fei; Yang, Tsang-Hsiung; Yang, Li-Ming [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 5, p. 2697 - 2706]
[39]Current Patent Assignee: ENDORECHERCHE, INC. - WO2005/66194, 2005, A1 Location in patent: Page/Page column 196-197
[40]Location in patent: scheme or table Wang, Yan-Xiang; Wang, Yu-Ping; Zhang, Hao; Kong, Wei-Jia; Li, Ying-Hong; Liu, Fei; Gao, Rong-Mei; Liu, Ting; Jiang, Jian-Dong; Song, Dan-Qing [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 6004 - 6008]
[41]Location in patent: experimental part Fournier, Diane; Poirier, Donald [European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4227 - 4237]
[42]Location in patent: experimental part Ma, Lei; Yang, Zhengyi; Li, Chenjing; Zhu, Zhiyuan; Shen, Xu; Hu, Lihong [Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol. 26, # 5, p. 643 - 648]
[43]Current Patent Assignee: PUSAN NATIONAL UNIVERSITY - US2014/37564, 2014, A1 Location in patent: Paragraph 0314-0315
[44]Tangdenpaisal, Kassrin; Worayuthakarn, Rattana; Karnkla, Supatra; Ploypradith, Poonsakdi; Intachote, Pakamas; Sengsai, Suchada; Saimanee, Busakorn; Ruchirawat, Somsak; Chittchang, Montakarn [Chemistry - An Asian Journal, 2015, vol. 10, # 4, p. 925 - 937]
[45]Xi, Meiyang; Ge, Jun; Wang, Xiaojian; Sun, Chenbin; Liu, Tianqi; Fang, Liang; Xiao, Qiong; Yin, Dali [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 14, p. 3218 - 3230]
[46]Van der Walt, Mietha M.; Terre'Blanche, Gisella; Petzer, Jacobus P.; Petzer, Anél [European Journal of Medicinal Chemistry, 2017, vol. 125, p. 1193 - 1199]
[47]Cao, Jiangying; Ma, Chunhua; Zang, Jie; Gao, Shuai; Gao, Qianwen; Kong, Xiujie; Yan, Yugang; Liang, Xuewu; Ding, Qin'ge; Zhao, Chunlong; Wang, Binghe; Xu, Wenfang; Zhang, Yingjie [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3145 - 3157]
[48]Liu, Jianwen; Ma, Lei; Shi, Ximeng; Yin, Huanhuan; Zhao, Yuyu; Zhou, Licheng [Letters in drug design and discovery, 2020, vol. 17, # 10, p. 1270 - 1282]
[49]Current Patent Assignee: PROTECH - EP3828164, 2021, A1 Location in patent: Paragraph 0112-0113
[50]Wang, Hui; Yang, Ren-Yin; Xu, Bo [Chemistry - A European Journal, 2022, vol. 28, # 23]

7
[ 1700-37-4 ]
[ 1779-58-4 ]
[ 129649-12-3 ]
cis-methyl 3-(3-benzyloxyphenyl)propenoate [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1272 - 1278
[2]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1272 - 1278

8
[ 16357-40-7 ]
[ 1700-37-4 ]
3-[(E)-3-(3-Benzyloxy-phenyl)-acryloyl]-4-hydroxy-benzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1075 - 1089

9
[ 1700-37-4 ]
[ 33208-99-0 ]
(S)-2-(3-Benzyloxy-benzylamino)-propionamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 579 - 590

10
[ 1700-37-4 ]
[ 85604-06-4 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 14021 - 14023
[2]Heterocycles,2001,vol. 54,p. 259 - 274

11
[ 141-82-2 ]
[ 1700-37-4 ]
[ 122024-75-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With piperidine; pyridine; at 120℃; for 3h;	General procedure: To themixture of the corresponding aldehyde (2.52 g, 12.7 mmol) andmalonic acid (1.99 g, 19.1 mmol), dry pyridine (6.5 ml) and piperidine(0.2 ml) were successively added. The mixture was stirred at120 C for 3 h, cooled to 10 C and acidified with HCl (~14 ml) at 1:1ratio with cooling and stirring. After 30 min, the precipitate wasfiltered, washed 3 times with H2O (20 ml) and air dried. The yieldsof o-, m- and p-PhO-CA were 92, 91 and 96%, respectively.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 183
[2]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S433 - S435

12
[ 1700-30-7 ]
[ 1700-37-4 ]

Yield	Reaction Conditions	Operation in experiment
98.5%	With potassium permanganate; zirconium(IV) oxychloride In tetrahydrofuran at 20℃; for 8h; ultrasonification;
95%	With 1,2-dimethyl-3-[3-(methylsulfinyl)propyl]-1H-imidazolium triflate; oxalyl dichloride; triethylamine In dichloromethane; acetonitrile at -78 - 20℃;
89%	With C₆H₄MoNO₇^(1-)*C₁₉H₄₂N⁽¹⁺⁾; oxygen In water at 100℃; for 18h; Green chemistry; chemoselective reaction;	2.3. General procedure for the catalytic oxidation of alcohols toaldehydes General procedure: A mixture of alcohol (0.75 mmol), and catalyst Mo1 (13 mg,3.0 mol%) taken in 0.5 mL of water was stirred at 100 ° C under oxygenatmosphere (O2 bladder) and the stirring was continued for16-24 h as per requirement. The progress of reaction was monitoredby TLC. After completion of the reaction, ethyl acetate was added to the mixture. The aqueous phase was extracted with ethyl acetate 2-3 times. Then the combined organic extracts were driedover anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product so obtained was purified by column chromatography using hexane-ethyl acetate as eluent. While the known products were characterized by spectroscopic techniques and compared with reported data and the new products 22b and 36b were characterized completely. The characterization detail is provided in supporting information section.

86%	With dipotassium peroxodisulfate; V₂O₅/TiO₂ In water; acetonitrile at 80℃; Sealed tube; Green chemistry;
83%	With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 1,4-dioxane at 80℃; Schlenk technique;	General Procedure-2 [For the open air oxidation of alcohols to carbonyl compounds; GP-2(method B)]: General procedure: In an oven dried Schlenk tube, were added alcohol 1 (69.0-199.5 mg, 0.5 mmol), CuI (10 mol%)and 1,10-Phenanthroline (20 mol%) and K3PO4 (2 mmol) followed by the addition of dioxane (2mL) at room temperature under open air atmosphere. The stirred reaction mixture was heated inan oil bath at 80 C for 7-48 h. Progress of the reaction was monitored by TLC till the reaction iscompleted. Then, the reaction mixture was cooled to room temperature, quenched with aqueousNH4Cl solution and then extracted with CH2Cl2 (3 10 mL). The organic layer was washed withsaturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent under reducedpressure and purification of the crude material by silica gel column chromatography (petroleumether/ethyl acetate) furnished the aldehyde/ketone 2 (61-97%).
71%	With oxalyl dichloride; polystyrene bound sulfoxide reagent; triethylamine In dichloromethane at -60 - -40℃; for 2.5h;
56%	With cerium(III) chloride heptahydrate; sodium hydrogencarbonate In acetonitrile at 50℃; for 35h; Irradiation; Sealed tube;	General procedure (GP1) General procedure: A 10 mL glass vial equipped with a teflon-coated stirring bar was charged with benzylic alcohol 1 (0.2 mmol), CeCl3·7H2O (10 mol %), and NaHCO3 (10 mol%). The glass vial was sealed with a PTFE septum. Then, solvent (2 mL) was added and the reaction was opened to air via a needle. The reaction was placed in a pre-programed temperature (50 °C) controlled blue LED reactor (as shown in Figure S1) and the reaction mixture was irradiated with a 455 nm blue LED. After 35-48 hours, the reaction mixture was concentrated under reduced pressure. Product 2 was purified by flash chromatography on silica using hexane and AcOEt.

Reference： [1]Zhang, Wei-Ge; Zhao, Rui; Ren, Jian; Ren, Li-Xiang; Lin, Jin-Guang; Liu, Dai-Lin; Wu, Ying-Liang; Yao, Xin-Sheng [Archiv der Pharmazie, 2007, vol. 340, # 5, p. 244 - 250]
[2]He, Xun; Chan, Tak Hang [Tetrahedron, 2006, vol. 62, # 14, p. 3389 - 3394]
[3]Thiruvengetam, Prabaharan; Chakravarthy, Rajan Deepan; Chand, Dillip Kumar [Journal of Catalysis, 2019, vol. 376, p. 123 - 133]
[4]Upadhyay, Rahul; Kumar, Shashi; Maurya, Sushil K. [ChemCatChem, 2021, vol. 13, # 16, p. 3594 - 3600]
[5]Reddy, Alavala Gopi Krishna; Mahendar, Lodi; Satyanarayana, Gedu [Synthetic Communications, 2014, vol. 44, # 14, p. 2076 - 2087]
[6]Cole, Derek C; Stock, Joseph R; Kappel, Jo Anne [Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 14, p. 1791 - 1793]
[7]König, Burkhard; Kumar, Sumit; Stahl, Jessica; Yatham, Veera Reddy; Yedase, Girish Suresh [Beilstein Journal of Organic Chemistry, 2021, vol. 17, p. 1727 - 1732]

13
[ 503-87-7 ]
[ 1700-37-4 ]
(Z)-5-(3-(benzyloxy)benzylidene)-2-thioxoimidazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium acetate; acetic acid at 20℃; for 25.5h; Reflux;
74%	With sodium acetate; acetic acid for 2h; Heating;
57.4%	With sodium acetate; acetic acid for 4h; Reflux;	11.5; 11-16 Synthesis of (Z)-5-(3-(benzyloxy)benzylidene)-2- thioxoimidazolidin-4-one (Compound 138) General procedure: [0291] In an acetic acid (AcOH) (1.53 ml/10 eq. of sodium acetate) solvent, a solution including sodium acetate (3.0 to 10.0 eq.), 3-(benzyloxy)benzaldhehyde Compound 123a, 1.0 eq., used for the synthesis of 3-(benzyloxy)benzylidene analogue) or 4-(benzyloxy)benzaldhehyde (Compound 123b, 1.0 eq., used for the synthesis of 4-(benzyloxy)benzylidene analogue) and rhodanine (1.1 eq., used for the synthesis of Compounds 128 and 137), 2,4-thiazolidinedione (1.1 eq., used for the synthesis of Compounds 125 and 134), 2-thio- hydantoin(1.1 eq., used for the synthesis of Compounds 130 and 138), or pseudothiohydantoin (1.1 eq., used for the synthesis of Compounds 131 and 139) was refluxed. After cooling, water was added thereto. The produced precipitate was filtered and washed with water and a co-solvent of hexane and ethyl acetate (1:1) to obtain a solid target compound. [0308] A reaction time of 4 hours; a yield of 57.4%; ‘HNMR (500 MHz, DMSO-d5) ö 12.37 (s, 1H), 12.18 (s, 1H),7.46 (d, 2H, J=7.5 Hz), 7.39 (t, 2H, J=7.5 Hz), 7.35-7.3 1 (m,4H), 7.02 (brd, 1H, J=8.OHz), 6.44 (s, 1H), 5.16 (s, 2H); ‘3CNMR (100 MHz, DMSO-d5) ö 180.0, 166.5, 159.2, 137.6,134.3, 130.6,129.1, 128.6,128.5, 128.5,123.7, 116.7,116.6,112.2, 70.0;

57.4%	With sodium acetate; acetic acid for 4h; Reflux;	11-16 Synthesis of (Z)-5-(3-(benzyloxy)benzylidene)-2-thioxoimidazolidin-4-one General procedure: In an acetic acid (AcOH) (1.53 mL/10 eq. of sodium acetate) solvent, a solution including sodium acetate (3.0 to 10.0 eq.), 3-(benzyloxy)benzaldhehyde Compound 123a, 1.0 eq., used for the synthesis of 3-(benzyloxy)benzylidene analogue) or 4-(benzyloxy)benzaldhehyde (Compound 123b, 1.0 eq., used for the synthesis of 4-(benzyloxy)benzylidene analogue) and rhodanine (1.1 eq., used for the synthesis of Compounds 128 and 137), 2,4-thiazolidinedione (1.1 eq., used for the synthesis of Compounds 125 and 134), 2-thiohydantoin (1.1 eq., used for the synthesis of Compounds 130 and 138), or pseudothiohydantoin (1.1 eq., used for the synthesis of Compounds 131 and 139) was refluxed. After cooling, water was added thereto. The produced precipitate was filtered and washed with water and a co-solvent of hexane and ethyl acetate (1:1) to obtain a solid target compound.
	Reflux;

Reference： [1]Kaczor, Aneta; Szemerédi, Nikoletta; Kucwaj-Brysz, Katarzyna; Dąbrowska, Monika; Starek, Małgorzata; Latacz, Gniewomir; Spengler, Gabriella; Handzlik, Jadwiga [ChemMedChem, 2021, vol. 16, # 15, p. 2386 - 2401]
[2]Kiec-Kononowicz; Szymanska [Il Farmaco, 2003, vol. 57, # 11, p. 909 - 916]
[3]Current Patent Assignee: PUSAN NATIONAL UNIVERSITY - US2014/23603, 2014, A1 Location in patent: Paragraph 0291; 0308
[4]Current Patent Assignee: PUSAN NATIONAL UNIVERSITY - KR101677122, 2016, B1 Location in patent: Paragraph 0454-0455; 0489
[5]Rempel; Atzler; Behrenswerth; Karcz; Schoeder; Hinz; Kaleta; Thimm; Kiec-Kononowicz; Müller [MedChemComm, 2014, vol. 5, # 5, p. 632 - 649]

14
[ 1700-37-4 ]
[ 76-05-1 ]
[ 177911-87-4 ]
<i>C</i>-[1-(3-benzyloxy-benzyl)-pyrrolidin-2-yl]-methylamine; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 2723 - 2737

15
[ 1700-37-4 ]
[ 76-05-1 ]
[ 162167-97-7 ]
{1-[3-(benzyloxy)benzyl]piperidin-3-yl}methanamine bis(trifluoroacetate) salt [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 2723 - 2737

16
[ 1700-37-4 ]
[ 32004-66-3 ]
{3-[1-(3-Benzyloxy-phenyl)-meth-(E)-ylidene]-6-fluoro-2-methyl-3H-inden-1-yl}-acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5-fluoro-2-methyl-1H-indene-3-acetic acid With 2-chlorotrityl chloride resin; N-ethyl-N,N-diisopropylamine In dichloromethane at 21℃; for 2h; Stage #2: 3-Benzyloxybenzaldehyde With 1,8-diazabicyclo[5.4.0]undec-7-ene at 60℃; Stage #3: With trifluoroacetic acid In dichloromethane

Reference： [1]Mueller, Oliver; Gourzoulidou, Eleni; Carpintero, Mercedes; Karaguni, Ioanna-Maria; Langerak, Anette; Herrmann, Christian; Moeroey, Tarik; Klein-Hitpass, Ludger; Waldmann, Herbert [Angewandte Chemie - International Edition, 2004, vol. 43, # 4, p. 450 - 454]

17
[ 1700-37-4 ]
[ 22483-09-6 ]
[ 7651-83-4 ]

Reference： [1]Chemical Communications,2005,p. 2208 - 2210
[2]Journal of the American Chemical Society,2011,vol. 133,p. 12451 - 12453

18
[ 141-82-2 ]
[ 1700-37-4 ]
3-amino-3-(3-(benzyloxy)phenyl)propanoic acid [ No CAS ]
[ 122024-75-3 ]

Reference： [1]Russian Journal of General Chemistry,2005,vol. 75,p. 1113 - 1124

19
[ 79678-37-8 ]
[ 1700-37-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 88.9 percent / NaBH₄; I₂ / tetrahydrofuran / 6 h / 70 °C 2: 98.5 percent / KMnO₄; ZrOCl₂*8H₂O / tetrahydrofuran / 8 h / 20 °C / ultrasonification

Reference： [1]Zhang, Wei-Ge; Zhao, Rui; Ren, Jian; Ren, Li-Xiang; Lin, Jin-Guang; Liu, Dai-Lin; Wu, Ying-Liang; Yao, Xin-Sheng [Archiv der Pharmazie, 2007, vol. 340, # 5, p. 244 - 250]

20
[ 1700-37-4 ]
[ 91523-50-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 47 - 50
[2]Journal of Medicinal Chemistry,1984,vol. 27,p. 1321 - 1325

21
[ 1700-37-4 ]
[ 900800-02-4 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 3101 - 3110

22
[ 1700-37-4 ]
[ 20967-96-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2205 - 2208

23
[ 1700-37-4 ]
[ 7651-83-4 ]

Reference： [1]Synthetic Communications,1999,vol. 29,p. 1617 - 1625
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 4983 - 4994

24
[ 1700-37-4 ]
[ 1700-31-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 941 - 944
[2]Journal of Organic Chemistry,1994,vol. 59,p. 5999 - 6007
[3]Journal of Medicinal Chemistry,1993,vol. 36,p. 2950 - 2955
[4]Tetrahedron,1992,vol. 48,p. 819 - 830
[5]Journal of the Chemical Society,1965,p. 3645 - 3660
[6]European Journal of Medicinal Chemistry,2011,vol. 46,p. 4227 - 4237

25
[ 1700-37-4 ]
[ 155697-42-0 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820

26
[ 22272-48-6 ]
[ 100-39-0 ]
[ 100-83-4 ]
[ 1700-37-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In methanol; chloroform; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran;	3-Benzyloxy-benzaldehyde (32) To a solution of 3-hydroxylbenzaldehyde 31 (5.0 g, 40 mmol) and K2CO3 (27.2 g, 197 mmol) in 200 ml CHCl3: 100 ml MeOH was added benzylbromide (5.9 ml, 49 mmol). The suspension was refluxed under nitrogen overnight. The solvent was removed by evaporation and the resulting oil was taken up in DCM and washed with water and brine and dried (Na2SO4). The crude product was purified by column chromatography to yield the product as a viscous oil which solidified upon sitting (8.48 g, 40 mmol, 98%). m.p. 46. 1H NMR (500 MHz, CDCl3) delta9.97 (s, 1 H), 7.48-7.25 (m, 9 H), 5.13 (s, 2 H). 13C NMR (125 MHz, CD3OD) delta191.8, 159.2, 137.8, 136.3, 130.0, 128.6, 128.1, 127.5, 123.41, 121.9, 113.3, 70.0. HRMS (EI) m/e calcd for C14H12O2: 212.08373, found: 212.0827.

Reference： [1]Patent: US2003/8882,2003,A1

27
[ 1700-37-4 ]
[ 6622-92-0 ]
(E)-2-[2-(3-benzyloxy-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	In acetic anhydride;	b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (2 g, 16.1 mmol) and 3-benzyloxybenzaldehyde (3.42 g, 16.1 mmol) in acetic anhydride there was obtained (E)-2-[2-(3-benzyloxy-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol (2.8 g, 54%) as a off-white solid. EI mass spectrum, m/e: 318 (M calculated for C20H18N2O2: 318).

Reference： [1]Patent: US2002/86858,2002,A1

28
[ 60-29-7 ]
[ 1700-37-4 ]
[ 104566-41-8 ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium borohydrid; In ethanol; ammonia; water;	REFERENTIAL EXAMPLE 1 Production of 3-benzyloxybenzylamine hydrochloride Three hundred milligrams of 3-benzyloxybenzaldehyde was dissolved in 15% ammonia/ethanol, and the solution was stirred for 3 hours. Then, 100 mg of sodium borohydride was added, and the mixture was stirred for 1 hour. The reaction mixture was distilled under reduced pressure, and 20 ml of water and 20 ml of ethyl ether were added. The organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and the solvent was evaporated. The residue was recrystallized from a mixture of tetrahydrofuran and ethyl ether containing hydrogen chloride to give 140 mg (yield 40%) of the captioned compound as colorless scales having a melting point of 155 to 159 C.

Reference： [1]Patent: US5234946,1993,A

29
[ 1700-37-4 ]
[ 593-56-6 ]
o-methylaldoxime [ No CAS ]
[ 104566-41-8 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In ethanol; water;	REFERENCE EXAMPLE 2A 3-Benzyloxybenzylamine hydrochloride A mixture comprising 12.72 g of 3-benzyloxybenzaldehyde, 5.76 g of O-methylhydroxylamine hydrochloride, 9.49 g of pyridine and 130 ml of ethanol was refluxed under stirring for 1.5 hours. The solvent was distilled off under reduced pressure, and water was added to the residue. The mixture was extracted with benzene. The extract was washed with water (twice) and a saturated sodium chloride aqueous solution, and dried over sodium sulfate, and then the solvent was distilled off to obtain O-methylaldoxime as pale yellow crystals. NMR(CDCl3)6: 7.97 (1H, s), 7.33 (5H, s), 7.5-6.8 (4H, m), 5.03 (2H, s), 3.92 (3H, s).

Reference： [1]Patent: US5098900,1992,A

30
[ 14690-00-7 ]
[ 1700-37-4 ]
5-Benzyloxy-2-(3-benzyloxyphenyl)-1,3-dioxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In benzene	16 5-Benzyloxy-2-(3-benzyloxyphenyl)-1,3-dioxane EXAMPLE 16 5-Benzyloxy-2-(3-benzyloxyphenyl)-1,3-dioxane A mixture of 2-benzyloxy-1,3-propanediol (18.0 g, 0.1 mole), 3-benzyloxybenzaldehyde (21.2 g, 0.1 mole) and p-toluenesulfonic acid (0.1 gram) in 150 ml of benzene was heated at reflux under a Dean-Stark apparatus until collection of water ceased (1.8 ml). The solution was washed with 2% sodium bicarbonate (2 * 100 ml) and with water (2 * 100 ml), then dried over magnesium sulfate and concentrated to give 34.2 g of brown oil. Recrystallization from benzene-ligroin gave 22.5 g of solid, m.p. 77°-78° C. nmr analysis of this solid indicated it to contain 31% cis-5-benzyloxy-2-(3-benzyloxyphenyl)-1,3-dioxane.

Reference： [1]Current Patent Assignee: FMC CORP - US4077982, 1978, A

31
[ 1700-37-4 ]
[ 171861-74-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-Benzyloxybenzaldehyde With ammonia; iodine at 20℃; for 1h; Stage #2: With urea hydrogen peroxide adduct; potassium carbonate In tetrahydrofuran at 20℃;

Reference： [1]Location in patent: scheme or table Zeng, Li-Fan; Zhang, Hu-Shan; Wang, Yun-Hua; Sanchez, Tino; Zheng, Yong-Tang; Neamati, Nouri; Long, Ya-Qiu [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4521 - 4524]

32
[ 75-52-5 ]
[ 1700-37-4 ]
[ 169394-83-6 ]

Yield	Reaction Conditions	Operation in experiment
66%	With ammonium acetate for 1h; Reflux; Inert atmosphere;	38.B A solution of the product of Step A (1.33 g; 6.3 mmol) and NH4OAc (0.5 g; 6.5 mmol) in CH3NO2 (12 ml) was refluxed for 1 h under N2. After evaporation of the solvent under reduced pressure, the residue was purified by crystallization from MeOH to give the title compound (1 .06 g; 66%), as yellow crystals. 1H-NMR (CDCI3 ) 3.47 (d, 1 H, J = 5.2 Hz); 5.09 (s, 2H); 7.1 - 7.15 (m, 3H); 7.32 - 7.42 (m, 5H); 7.52 (d, 1 H, J = 13.6 Hz); 7.94 (d, 1 H, J = 13.6 Hz).

Reference： [1]Current Patent Assignee: AKAAL PHARMA - WO2010/42998, 2010, A1 Location in patent: Page/Page column 98

33
[ 1700-37-4 ]
[ 6640-09-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium / methanol / 12 h / 0 °C 2: 5,5-dimethyl-1,3-cyclohexadiene / 1 h / Reflux 3: sodium hydroxide / methanol / 1 h / 60 °C

Reference： [1]Choi, Taeyoung; Ma, Eunsook [Molecules, 2010, vol. 15, # 11, p. 7971 - 7984]

34
[ 1700-37-4 ]
[ 22877-01-6 ]
C₃₆H₃₀O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In ethanol; water; at 20℃;	General procedure: The commercially available hydroxyacetophenone (1.0 mmol) was dissolved inethanol (10ml) with 20% aqueous potassium hydroxide solution (1ml), then theappropriate benzaldehyde (1.0 mmol) was added drop by drop to the mixture. Thesolution was stirred at room temperature for 6-12 h to prepare compounds 1-7. Thepiperidine (0.5 ml) was used as a catalyst at 80 C to obtain compounds 8-15.Compounds 16-18 were synthesized via the condensation of the hydroxyl-protectedstarting materials and deprotected subsequently. The reaction progress was monitoredusing silica gel TLC with Petroleum ether/EtOAc as mobile phase. Upon completion,the mixture was poured into water and adjusted to pH 5, which was extracted with 3 × 30 mL of EtOAc, washed with brine, dried over anhydrous Na2SO4 and purified bychromatography (PE/EA) on silica gel.

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2011,vol. 26,p. 643 - 648
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 3602 - 3606

35
[ 1700-37-4 ]
[ 60480-83-3 ]
[ 391646-69-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium acetate; In ethanol; water; at 75℃; for 0.166667h;	To a stirred suspension of <strong>[60480-83-3]2,4-dimethylphenylhydrazine hydrochloride</strong> (2.68 g, 15.54 mmol) and sodium acetate (1.27 g, 15.54 mmol) in water (20 mL) was added 3 (3.0 g, 14.1 mmol) portionwise, followed by EtOH (10 mL). The reaction mixture was heated to 75 C and held at this temperature for 10 min with vigorous stirring until yellow solid precipitated. The mixture was cooled to 0 C and filtered. The solid was washed with cold water, hexanes and dried to afford 4 (4.25 g, 91%) as a yellow solid, which was stored at -20 C; mp 70-71 C. 1H NMR (DMSO-d6): delta 9.48 (s, 1H), 8.05 (s, 1H), 7.48 (d, J = 7.5 Hz, 2H), 7.40 (t, J = 7.5 Hz, 2H), 7.35-7.28 (m, 4H), 7.19 (d, J = 7.5 Hz, 1H), 6.95-6.92 (m, 2H), 6.86 (s, 1H), 5.15 (s, 2H), 2.19 (s, 3H), 2.18 (s, 3H). 13C NMR (DMSO-d6): delta 158.7, 140.9, 137.5, 137.1, 137.0, 130.9, 129.7, 128.4, 127.8, 127.7, 127.4, 127.1, 120.7, 118.6, 114.5, 112.4, 111.1, 69.2, 20.2, 17.4. HRMS (ESI-TOF, m/z): calcd for C22H23N2O ([M+H]+) 331.1800; found 331.1810.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 524 - 527

36
[ 1700-37-4 ]
[ 100-83-4 ]
[ 2687-12-9 ]
[ 192457-33-3 ]

Yield	Reaction Conditions	Operation in experiment
79%		13 5.1.13 3-Cinnamyloxybenzaldehyde (15) To the solution of the 3-hydroxybenzaldehyde (1.43 g, 11.69 mmol) in acetonitrile were added benzyl bromide (2.0 g, 11.69 mmol) and potassium carbonate (3.23 g, 23.38 mmol) and stirred for 14 h at room temperature. After the completion of reaction, as indicated by TLC, solvent was removed in vacuo, the residue was diluted with water and extracted with ethyl acetate (3 × 20 mL). The separated organic layers were dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The residual oil was purified by flash chromatography (n-hexane/ethyl acetate 95:5) to yield compound 14. Following the procedure as described for 14, starting with 3-hydroxybenzaldehyde (1.60 g, 13.10 mmol) and cinnamyl chloride (2.0 g, 13.10 mmol), compound 15 (2.46 g, 79%) was obtained as pale yellow solid; Rf = 0.62 (n-hexane/ethyl acetate 95:5); 1H NMR (400 MHz; CDCl3; TMS) δ 9.98 (1H, s), 7.41-7.48 (6H, m), 7.34 (3H, m), 6.76 (1H, d, J = 15.9 Hz), 6.42 (1H, dt, J = 16.1 Hz, 5.8 Hz), 4.77 (2H, d, J = 5.8 Hz); 13C NMR (100 MHz, CDCl3, TMS) δ 192.22, 159.14, 137.76, 136.21, 133.49, 130.13, 128.62, 128.05, 126.60, 123.68, 123.64, 122.15, 113.12, 68.64.

Reference： [1]Patel, Bhargav A.; Krishnan, Ramalingam; Khadtare, Nikhil; Gurukumar; Basu, Amartya; Arora, Payal; Bhatt, Aaditya; Patel, Maulik R.; Dana, Dibyendu; Kumar, Sanjai; Kaushik-Basu, Neerja; Talele, Tanaji T. [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 3262 - 3271]

37
[ 1700-37-4 ]
[ 122-07-6 ]
(3-benzyloxybenzyl)-(2,2-dimethoxyethyl)methylamine [ No CAS ]

Reference： [1]Organic Process Research and Development,2007,vol. 11,p. 1043 - 1050

38
[ 1700-37-4 ]
[ 587-33-7 ]

Reference： [1]Organic Process Research and Development,2007,vol. 11,p. 1069 - 1075
[2]Organic Process Research and Development,2007,vol. 11,p. 1069 - 1075

39
[ 75-15-0 ]
[ 4461-39-6 ]
[ 1700-37-4 ]
[ 6046-93-1 ]
C₄₀H₄₆CuN₄O₄S₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%		To a round-bottom flask (250 mL) containing 3-(benzyloxy)benzaldehyde (3.50 g, 16.5 mmol) dissolved in methanol (100 ml), N-(2-Hydroxyethyl)-1,3-propanediamine (3.50 g, 16.5 mmol) was added. The resulting mixture was stirred for 2 h at ambient temperature. Then carbon disulfide (1.00 mL, 16.5 mmol) was slowly mixed to the reaction, which was kept under stirring for about 40 min. Cu(O2CCH3)2H2O (1.50 g, 8.25 mmol) was then added and a brown solid was formed. After stirring for 4 h, the formed brown precipitate was filtrated and re-crystallized in a 4:1 mixture of CH2Cl2 and toluene. Yield 81%. Mp. 93.6-95.0 C. IR (cm-1, KBr): 1496 (nuN-CS); 980 {nuasym(C-S)}; 601 {nusym(C-S)}. Analysis of C, H and N, respectively for C40H48N4O4S4Cu found% (calc.%): 56.95 (57.15); 5.67 (5.76); 6.58 (6.66).

Reference： [1]Journal of Molecular Structure,2013,vol. 1048,p. 357 - 366

40
[ 1700-37-4 ]
[ 556-90-1 ]
[ 1393445-42-5 ]

Yield	Reaction Conditions	Operation in experiment
43.2%	With sodium acetate; acetic acid; for 3h;Reflux;	General procedure: [0291] In an acetic acid (AcOH) (1.53 ml/10 eq. of sodium acetate) solvent, a solution including sodium acetate (3.0 to 10.0 eq.), 3-(benzyloxy)benzaldhehyde Compound 123a, 1.0 eq., used for the synthesis of 3-(benzyloxy)benzylidene analogue) or 4-(benzyloxy)benzaldhehyde (Compound 123b, 1.0 eq., used for the synthesis of 4-(benzyloxy)benzylidene analogue) and rhodanine (1.1 eq., used for the synthesis of Compounds 128 and 137), 2,4-thiazolidinedione (1.1 eq., used for the synthesis of Compounds 125 and 134), 2-thio- hydantoin(1.1 eq., used for the synthesis of Compounds 130 and 138), or <strong>[556-90-1]pseudothiohydantoin</strong> (1.1 eq., used for the synthesis of Compounds 131 and 139) was refluxed. After cooling, water was added thereto. The produced precipitate was filtered and washed with water and a co-solvent of hexane and ethyl acetate (1:1) to obtain a solid target compound. [0309] A reaction time of 3 hours; a yield of 43.2%; ?HNMR (400 MHz, DMSO-d5) oe 9.42 (s, 1H), 9.13 (s, 1H), 7.53(s, 1H), 7.43 (d, 2H, J=7.6 Hz), 7.41-7.35 (m, 3H), 7.30 (t, 1H,J=7.6 Hz), 7.19 (d, 1H, J=1.6 Hz), 7.12 (d, 1H, J=8.0 Hz),7.05 (dd, 1H, J=1.6, 8.4 Hz), 5.12 (s, 2H); ?3C NMR (100MHz, DMSO-d5) oe 180.9, 176.2, 159.4, 137.4, 136.2, 131.0,130.4, 129.6, 129.2, 128.6, 128.5, 122.4, 116.9, 116.3, 70.0.
43.2%	With sodium acetate; acetic acid; for 3h;Reflux;	General procedure: In an acetic acid (AcOH) (1.53 mL/10 eq. of sodium acetate) solvent, a solution including sodium acetate (3.0 to 10.0 eq.), 3-(benzyloxy)benzaldhehyde Compound 123a, 1.0 eq., used for the synthesis of 3-(benzyloxy)benzylidene analogue) or 4-(benzyloxy)benzaldhehyde (Compound 123b, 1.0 eq., used for the synthesis of 4-(benzyloxy)benzylidene analogue) and rhodanine (1.1 eq., used for the synthesis of Compounds 128 and 137), 2,4-thiazolidinedione (1.1 eq., used for the synthesis of Compounds 125 and 134), 2-thiohydantoin (1.1 eq., used for the synthesis of Compounds 130 and 138), or <strong>[556-90-1]pseudothiohydantoin</strong> (1.1 eq., used for the synthesis of Compounds 131 and 139) was refluxed. After cooling, water was added thereto. The produced precipitate was filtered and washed with water and a co-solvent of hexane and ethyl acetate (1:1) to obtain a solid target compound.

Reference： [1]Patent: US2014/23603,2014,A1 .Location in patent: Paragraph 0291; 0309
[2]Patent: KR101677122,2016,B1 .Location in patent: Paragraph 0454-0455; 0491

41
[ 1700-37-4 ]
[ 34068-01-4 ]
C₂₉H₂₆O₃ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 946 - 950

42
[ 1700-37-4 ]
[ 34068-01-4 ]
C₂₉H₂₄O₃ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 946 - 950

43
[ 2879-20-1 ]
[ 1700-37-4 ]
5-(3-(benzyloxy)phenyl)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-phenyl-4,5-dihydro-1H-pyrazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3052 - 3061

44
[ 2879-20-1 ]
[ 1700-37-4 ]
C₂₄H₂₀O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; at 20℃;	General procedure: To <strong>[2879-20-1]1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethan-1-one</strong>(A) (1 mmol) alcohol solution (5 mL) was added substituted benzaldehyde(1 mmol). After dissolution, 50% NaOH (0.5 mL) was added. After confirming the completion of the reaction by thin layer chromatography, the sediment was filtered, washed with ethanol and dried to obtain chalcone

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3052 - 3061

45
[ 1700-37-4 ]
[ 2234-16-4 ]
(E)-3-(3-(benzyloxy)phenyl)-1-(2,4-dichlorophenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium hydroxide In ethanol; water at 20℃; for 8h;	3 General procedure for synthesis of various substituted (E)-3-(3-(benzyloxy)phenyl)-1-phenylprop-2-en-1-ones (15a-15k) General procedure: Equimolar mixture of 3-(benzyloxy)benzaldehyde (13) and substituted acetophenones (14a-14k) was reacted in the presence of 50% (w/v) KOH/H2O using ethanol as a solvent. The reaction mixture was stirred at room temperature for 8-24h. The reaction mixture was poured into crushed ice (250g) and left for few hours. To this solution/suspension 1N HCl (10mL), was added until the solution was acidic. The resulting crude solid precipitate was collected by filtration and dried. Purification was done by recrystallization in CH3OH or a mixture of CH3OH and EtOAc with acceptable yields ranging from 70 to 85%.

Reference： [1]Manivannan, Elangovan; Amawi, Haneen; Hussein, Noor; Karthikeyan, Chandrabose; Fetcenko, Aubry; Narayana Moorthy, N.S. Hari; Trivedi, Piyush; Tiwari, Amit K. [European Journal of Medicinal Chemistry, 2017, vol. 133, p. 365 - 378]

46
[ 2142-69-0 ]
[ 1700-37-4 ]
(E)-3-(3-(benzyloxy)phenyl)-1-(2-bromophenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium hydroxide In ethanol; water at 20℃; for 8h;	8 General procedure for synthesis of various substituted (E)-3-(3-(benzyloxy)phenyl)-1-phenylprop-2-en-1-ones (15a-15k) General procedure: Equimolar mixture of 3-(benzyloxy)benzaldehyde (13) and substituted acetophenones (14a-14k) was reacted in the presence of 50% (w/v) KOH/H2O using ethanol as a solvent. The reaction mixture was stirred at room temperature for 8-24h. The reaction mixture was poured into crushed ice (250g) and left for few hours. To this solution/suspension 1N HCl (10mL), was added until the solution was acidic. The resulting crude solid precipitate was collected by filtration and dried. Purification was done by recrystallization in CH3OH or a mixture of CH3OH and EtOAc with acceptable yields ranging from 70 to 85%.

47
[ 1700-37-4 ]
[ 50479-11-3 ]
C₂₀H₂₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (3-ethoxycarbonylpropyl)triphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran for 1h; Cooling with ice; Stage #2: 3-Benzyloxybenzaldehyde In tetrahydrofuran at 20℃; for 48h;	Chemical Synthesis of 5-(3,4,5-Trihydroxyphenyl)valericAcid (EGC-M9) General procedure: Five milliliters of dichloromethane wasadded to 3,4,5-tribenzyloxybenzylalcohol (2.23 mmol, 950.5 mg,Tokyo Chemical Ind. Co., Ltd.) and Dess-Martin Periodinane(3.30 mmol, 1.4 g, Sigma-Aldrich Co., LCC) and the mixturewas stirred for 3 h at room temperature. The mixture wasadded to 5 mL of 5% sodium thiosulfate solution and was agitatedfor 30 min at room temperature. Next, the mixture wasextracted with 20 mL of ethyl acetate and the ethyl acetatelayer was washed with distilled water, the saturated NaHCO3solution, and saturated NaCl solution. After that, the organiclayer was dried with sodium sulfate and was filtered. Theresulting filtrate was evaporated to dryness and the crude residuecontaining 3,4,5-tribenzyloxybenzaldehyde (1.24 g) wasobtained. [3-(Ethoxycarbonyl)propyl]-triphenylphosphoniumBromide (4.38 mmol, 2.0 g, Wako Pure Chemical Industries,Ltd., Osaka, Japan) was added to 20 mL of anhydrous tetrahydrofuranand the mixture was stirred for 20 min on ice.Tetrahydrofuran containing sodium bis(trimethylsilyl)amide(5.83 mmol, 3.07 mL, Tokyo Chemical Ind. Co., Ltd.) wasthen added to the mixture and agitated for 1 h on ice. To theresulting solution was added 8 mL of tetrahydrofuran containing3,4,5-tribenzyloxybenzaldehyde (1.24 g synthesized above)and this was stirred for 48 h at room temperature. After adding30 mL of saturated ammonium chloride, the mixture wasextracted with 50 mL of diethyl ether. The organic layer waswashed with distilled water, saturated NaHCO3 solution, andsaturated NaCl solution and was dehydrated with sodiumsulfate. After removal of sodium sulfate by filtration, the filtratewas evaporated to dryness and the residue was addedto the mixed solution (hexane/diethyl ether, 150/50, v/v) andkept overnight at 4°C. After removal of insoluble materials,the filtrate was evaporated. The residue was dissolved in1 mL of the mobile phase (hexane/ethyl acetate (80/20, v/v))and applied to a silica-gel chromatography for purification.Silica-gel 60N (Kanto Chemical Co., Inc., Tokyo, Japan) ina column (20 i.d.×150 mm) was washed with 100 mL of themobile phase and then the sample was applied to the column.The fractions were analyzed by the TLC plate developed withhexane/ethyl acetate (80/20, v/v) as mobile phase and detectedwith UV light at 302 nm. The fractions containing ethyl-(Z)-5-(3,4,5-tribenzyloxyphenyl)-4-pentenoate were collected andconcentrated, and finally 1.91 mmol (942.0 mg) of the compoundwas obtained. The pentenoate was dissolved in 4 mL ofmethanol-tetrahydrofuran mixture. To the solution was added2 mL of 3 M KOH and this was stirred for 5 h at room temperature.Then, the reaction mixture was adjusted to pH 4.0 with2 M HCl and extracted with 20 mL of ethyl acetate. The ethylacetate layer was washed with distilled water and saturatedNaCl solution and was dehydrated with sodium sulfate. Afterfiltration, the filtrate was evaporated to dryness and 755.8 mgof the residue including (Z)-5-(3,4,5-tribenzyloxyphenyl)-4-pentenoic acid was obtained. The pentanoic acid was dissolvedin 8 mL of ethyl acetate and to the solution was added600.7 mg of Palladium (10 wt% (dry) on carbon powder, wet,Sigma-Aldrich Co., LCC). The mixture was replaced withargon gas and then was stirred for 6 h at room temperatureby injecting hydrogen gas. After filtration, the filtrate wasevaporated to dryness and the residue was dissolved in 10 mLof acetonitrile/distilled water/formic acid (5/95/0.1, v/v/v) andapplied to the preparative HPLC system as described previously.The preparative HPLC system, column, mobile phase,flow rate and absorbance were the same as the synthesis of5-(3,4-dihydroxyphenyl) levulinic acid. The column was initiallyeluted with 90% A and 10% B for 3 min, followed bylinear increases to 100% B from 3 to 15 min and held at 100%B for 5 min, then eluted with 90% A and 10% B from 20 to21 min, and finally equilibrated with 90% A and 10% B for5 min. The 5-(3,4,5-trihydroxyphenyl) valeric acid fraction wascollected, concentrated and finally 1.47 mmol (331.7 mg) of thecompound was obtained and its structure was confirmed byNMR analysis.

Reference： [1]Hara-Terawaki, Aya; Takagaki, Akiko; Kobayashi, Hirotsugu; Nanjo, Fumio [Biological and Pharmaceutical Bulletin, 2017, vol. 40, # 8, p. 1331 - 1335]

48
[ 100-39-0 ]
[ 99-06-9 ]
[ 1700-37-4 ]

Yield	Reaction Conditions	Operation in experiment
85.7%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;	12.1 (1) 3 - oxybenzylphenyl formaldehyde preparation The 3 - hydroxybenzaldehyde (1.0 g, 8.2 mmol) dissolved in 15 ml DMF in, adding [...] (1.52 g, 9.0 mmol), potassium carbonate (1.35 g, 9.8 mmol), 80 °C reaction 3 hours, adding 15 ml distilled water, extracted with ethyl acetate twice (2 × 20 ml), then saturated sodium chloride solution for washing 1 time, dried with anhydrous sodium sulfate. Concentrated, column chromatography, eluting agent is petroleum ether: ethyl acetate=3:1, to obtain white solid 1.5 g, yield 85.7%

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN107151220, 2017, A Location in patent: Paragraph 0246; 0247; 0248; 0249; 0250

49
[ 1700-37-4 ]
[ 1986-47-6 ]
(1S*,2R*)-N-(3-(benzyloxy)benzyl)-2-phenylcyclopropan-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%		General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 144,p. 52 - 67

50
[ 1700-37-4 ]
[ 15763-11-8 ]
(2R,3R,4S,5R)-2-(6-amino-2-(2-((E)-3-(benzyloxy)benzylidene)hydrazineyl)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	In methanol at 80℃; for 0.5h;	General procedure for the synthesis of compounds (12-43). General procedure: First, 0.5 g of 2-hydrazinoadenosine (11) and different aralkyl or alkylaldehyde compounds (1.1 equivalent) were combined in methanol(30 ml) and heated by microwave at 80 °C for 30 min. The crudeproducts (12-13, 17, 19, 21-32, and 35-39) were precipitated frommethanol, and the other products (14-16, 18, 20, 33-34, and 40-43) were purified from the reaction mixture using silica gel column chromatography. All the crude products were further purified by MPLC on reverse phase C18 material to yield the products(12-43).

Reference： [1]Zhang, Min; Fan, Shiyong; Zhou, Xinbo; Xie, Fei; Li, Song; Zhong, Wu [European Journal of Medicinal Chemistry, 2019, vol. 179, p. 310 - 324]

51
[ 19484-57-2 ]
[ 1700-37-4 ]
3,3′-((3′′-(benzyloxy)phenyl)methylene)bis(6-chloro-4-hydroxy-2H-chromen-2-one) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetraethylammonium bromide In water for 2h; Reflux;	4.2. General procedure for the syntheses of bis-coumarin derivatives 1-44 General procedure: 6-Fluoro-4-hydroxy /6-chloro-4-hydroxy /4-hydroxy coumarin(1 mmol), and a variety of aromatic aldehydes (0.5 mmol), as well as 10 mol% of tetraethylammonium bromide (TEAB) were dissolved indistilled water (15 mL) in a 100 mL round-bottommed flask. The reactionmixture was refluxed for 2 h. Periodic TLC was taken to check theprogress of reaction. Resulting precipitates were filtered, and washedwith distilled water. This afforded products 1-44 in high yields.

Reference： [1]Salar, Uzma; Nizamani, Arsalan; Arshad, Fizza; Khan, Khalid Mohammed; Fakhri, Muhammed Imran; Perveen, Shahnaz; Ahmed, Nessar; Choudhary, M. Iqbal [Bioorganic Chemistry, 2019, vol. 91]

52
[ 2010-15-3 ]
[ 1700-37-4 ]
(5Z)-5-(3-benzyloxybenzylidene)-3-phenyl-2-thioxo-4-imidazolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With piperidine In ethanol Reflux;	4.1.2 General procedure for the synthesis of (5Z)-3-aryl-5-arylidene-2-thioxo-4-imidazolidinones (7a-w) General procedure: A mixture of 3-aryl-2-thioxo-4-imidazolidinone 8 (2.6mmol), the appropriate arylaldehyde (2.6mmol) and piperidine (2.1mmol) in ethanol (20ml) was refluxed for 4-5h until the reagent disappearance. The reaction mixture was cooled and poured into water acidified with AcOH (pH 3-4). The precipitate was separated by filtration, washed with water and dried. The crystallization from methanol of the crude product provided pure compounds 7.

Reference： [1]Ottanà, Rosaria; Paoli, Paolo; Lori, Giulia; Adornato, Ilenia; Previti, Santo; Naß, Alexandra; Wolber, Gerhard; Maccari, Rosanna [Bioorganic Chemistry, 2019, vol. 92]

53
[ 1700-37-4 ]
[ 32004-66-3 ]
(Z)-2-(1-(3-(benzyloxy)benzylidene)-5-fluoro-2-methyl-1H-inden-3-yl)acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium methylate In methanol at 80℃; for 4h;

Reference： [1]Huang, Fengyu; Zeng, Zhiping; Zhang, Weidong; Yan, Zhiqiang; Chen, Jiayun; Yu, Liangfa; Yang, Qian; Li, Yihuan; Yu, Hongyu; Chen, Junjie; Wu, Caisheng; Zhang, Xiao-kun; Su, Ying; Zhou, Hu [European Journal of Medicinal Chemistry, 2021, vol. 222]

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• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Additions of Organometallic Reagents • Acetal Formation • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldehydes May Made by Terminal Alkynes Though Hydroboration-oxidation • Aldol Addition • Aldol Condensation • Alkenes React with Ozone to Produce Carbonyl Compounds • Alkylation of Aldehydes or Ketones • Amides Can Be Converted into Aldehydes • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Complex Metal Hydride Reductions • Conjugated Enone Takes Part in 1,4-Additions • Conversion of Amino with Nitro • Convert Aldonic Acid into the Lower Aldose by Oxidative Decarboxylation • Convert Esters into Aldehydes Using a Milder Reducing Agent • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Cyanohydrins can be Convert to Carbonyl Compounds under Basic Conditions • Deoxygenation of the Carbonyl Group • Deprotonation of a Carbonyl Compound at the α -Carbon • Deprotonation of Methylbenzene • DIBAL Attack Nitriles to Give Ketones • Directing Electron-Donating Effects of Alkyl • Dithioacetal Formation • Electrophilic Chloromethylation of Polystyrene • Enamine Formation • Enamines Can Be Used to Prepare Alkylated Aldehydes • Enol-Keto Equilibration • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Exclusive 1,4-Addition of a Lithium Organocuprate • Fischer Indole Synthesis • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Grignard Reaction • Grignard Reagents Transform Esters into Alcohols • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hantzsch Dihydropyridine Synthesis • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Henry Nitroaldol Reaction • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Horner-Wadsworth-Emmons Reaction • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydroboration of a Terminal Alkyne • Hydrogenation by Palladium on Carbon Gives the Saturated Carbonyl Compound • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • Lithium Organocuprate may Add to the α ,β -Unsaturated Carbonyl Function in 1,4-Fashion • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nitration of Benzene • Nomenclature of Ethers • Nozaki-Hiyama-Kishi Reaction • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alcohols to Carbonyl Compounds • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Passerini Reaction • Paternò-Büchi Reaction • Periodic Acid Degradation of Sugars • Petasis Reaction • Phenylhydrazone and Phenylosazone Formation • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Ethers • Primary Ether Cleavage with Strong Nucleophilic Acids • Prins Reaction • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reduction of an Ester to an Aldehyde • Reductive Amination • Reductive Removal of a Diazonium Group • Reformatsky Reaction • Reverse Sulfonation——Hydrolysis • Ring Opening of Oxacyclopropane • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Selective Eduction of Acyl Chlorides to Produce Aldehydes • Stetter Reaction • Stobbe Condensation • Strecker Synthesis • Sulfonation of Benzene • Synthesis of 2-Amino Nitriles • Synthesis of Alcohols from Tertiary Ethers • Tebbe Olefination • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • The Nitro Group Conver to the Amino Function • The Nucleophilic Opening of Oxacyclopropanes • The Wittig Reaction • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Ugi Reaction • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Historical Records

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[ 1700-37-4 ]

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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. 1700-37-4 ] {[proInfo.proName]}

Quality Control of [ 1700-37-4 ]

Related Doc. of [ 1700-37-4 ]

Product Details of [ 1700-37-4 ]

Calculated chemistry of [ 1700-37-4 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1700-37-4 ]

Application In Synthesis of [ 1700-37-4 ]

[ 1700-37-4 ] Synthesis Path-Upstream 1~24

[ 1700-37-4 ] Synthesis Path-Downstream 1~53

Technical Information

Related Functional Groups of [ 1700-37-4 ]

Aryls

Aldehydes

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1700-37-4 ]