4-Benzyloxy-3-hydroxybenzaldehyde

Pale Yellow Solid

N-(2-cvano- 1 -( 1 -hvdroxy-7-isopropoxy- 1.3-dihvdrobenzo [c] [ 1.2To a solution of 3, 4-dihydroxybenzaldehyde (2.03g, 14.7mmol) in acetone (150mL) was added KTo a solution of 3, 4-dihydroxybenzaldehyde (10.0 g, 72.4 mmol) and benzyl bromide (12.4 mmol, 72.4 mmol, 1.0 eq.) in acetone (400 mL) was added K3, 4-Dihydroxybenzaldehyde (10 g, 72.5 mmol) was dissolved in acetonitrile (150 mL).Add sodium bicarbonate (8 g, 94.3 mmol), warm to 60 ° C, add benzyl bromide (12.4 g, 72.5 mmol), Then the temperature was raised to 80 ° C and stirred overnight. The acetonitrile was removed by concentration, and 10percent aqueous hydrochloric acid (200 mL) was added to the residue.Extract with ethyl acetate (150 mL * 3), combine and dry.Filtration, concentration, and residue were purified by column chromatography to yield 10 g (yield: 60percent).0187] Benzyl bromide (9 mL, 0.073 mol, 1.05 eq) was added to a stirred solution of 3, 4-dihydroxybenzaldehyde (10 g, 0.07 mol, 1 eq), tetra-n-butylammonium iodide (29.4 g, 0.077 mol, 1.1 eq) and cesium carbonate (24.8 g, 0.073 mol, 1.05 eq) in N, N-dimethylformamide (200 mL). The reaction mixture was stirred overnight, and then concentrated in vacuo. The residual solution was diluted with ethyl acetate (200 mL) and washed with water (2.x.200 mL). The organic solution was then extracted with 0.5M aqueous sodium hydroxide (5.x.200 mL), and the basic extracts combined and washed with ethyl acetate (400 mL), then acidified to pH 1 with concentrated HCl and back extracted with ethyl acetate (2.x.300 mL). The organic extracts were combined, washed with brine (200 mL), dried over sodium sulfate and evaporated in vacuo. This gave a gummy solid, which was recrystallized from ethyl acetate and petroleum ether to give the product as a brown powder (8.4 g, 51percent). 1H NMR (CDCl3) δ 9.84 (s, 1H, OC-H), 5.84 (s, 1H, OH), 5.21 (s, 2H, CH2Ph).A mixture of 3, 4-dihydroxybenzaldehyde (1.38 g, 10 mmol), benzyl bromide (1.71 g, 10 mmol), and KAn ice cooled, stirred suspension of 60percent sodium hydride/oil (1.76 g, 44 mmol) in anhydrous DMF (40 mL) under nitrogen was treated dropwise with a solution of 3, 4-di-hydroxybenzaldehyde (5.525 g, 40 mmol) in anhydrous DMF (40 mL) and the mixture was stirred at room temperature for 30 min and recooled on an ice bath. Benzyl bromide (5.25 mL, 44 mmol) was then added via syringe and the mixture allowed to reach room temperature and stirred overnight (18 h). The mixture was combined with 1percent aqueous sodium hydroxide (300 mL) and the cloudy solution was extracted with ether (2 × 75 mL) and acidified with concentrated hydrochloric acid. A precipitate soon formed, and the resulting suspension was stirred for a few minutes and filtered. The solid was rinsed with water, partially air dried, dissolved in dichloromethane (100 mL), and dried (NaTo the solution of 3, 4-dihydroxybenzaldehyde (27, 285 mg, 2.00 mmol) in DMF (10 mL), NaHCOTo a solution of 3, 4-dihydroxybenzaldehyde (5.0 g, 36.2 mmol) in DMF (100 mL) at 0°C under N

Molecular Weight:228.24
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:228.078644241
Monoisotopic Mass:228.078644241
Topological Polar Surface Area:46.5
Heavy Atom Count:17
Complexity:236
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes