3,4-Dihydroxybenzaldehyde → 3-Hydroxy-4-[(4-methoxyphenyl)methoxy]benzaldehyde

Participants

Reaction Steps

4-Methoxybenzylchloride (20.6 mL, 0.14 mol, 1.05 eq) was added to a stirred solution of 3,4-dihydroxybenzaldehyde (20 g, 0.15 mol, 1 eq), tetra-n-butylammonium iodide (44.6 g, 0.12 mol, 0.8 eq) and cesium carbonate (35.4 g, 0.11 mol, 0.75 eq) in N,N-dimethylformamide (200 mL). The reaction mixture was stirred for 2 days, and then concentrated in vacuo. The residual solution was diluted with ethyl acetate (200 mL) and washed with 0.5M HCl (400 mL), water (4×200 mL) and saturated sodium chloride solution (200 mL), then 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 pale brown powder (21.29 g, 57%). 1H NMR (CDCl3) δ 9.84 (s, 1H, O═C—H), 5.80 (s, 1H, OH), 5.13 (s, 2H, CH2Ar), 3.85 (s, 3H, OCH3).

Provenance & Evidence