3-Benzyloxybenzaldehyde

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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). [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.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).[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, CDC1To 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; RREFERENTIAL A mixture of benzyl bromide (1.4 g; 8.2 mmol), 3-hydroxybenzaldehyde (1 .0 g; 8.2 mmol) and Cs3-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 MgSOGeneral 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).A mixture of 3-hydroxybenzaldehyde (3 g, 24.59 mmol), benzyl chloride (4.1 mL, 35.79 mmol) and anhydrous KStep 1 A suspension of 3-hydroxy benzaldehyde 11, benzyl chloride 12, KA 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).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

Molecular Weight:212.24
XLogP3:3.3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:212.083729621
Monoisotopic Mass:212.083729621
Topological Polar Surface Area:26.3
Heavy Atom Count:16
Complexity:209
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes