4-[(4-Methoxyphenyl)methoxy]-3-(phenylmethoxy)benzaldehyde → 3-Benzyloxy-4-hydroxybenzaldehyde

Participants

Reaction Steps

A solution of 4-[(4-Methoxyphenyl)methoxy]-3-(phenylmethoxy)benzaldehyde (25.93 g, 0.074 mol) in acetic acid (200 mL) was heated to reflux (150□C) and stirred for 2 days. The reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (200 mL). The organic solution was washed with water (200 mL) and 0.5M aqueous sodium hydroxide (5×200 mL). The basic extracts were combined, acidified to pH 1 with concentrated HCl and back extracted with ethyl acetate (2×300 mL). The organic solution was dried over sodium sulfate and evaporated in vacuo to a gummy solid, which was recrystallized from ethyl acetate and petroleum ether to give the product as a pale brown powder (14 g, 82%). 1H NMR (CDCl3) δ 9.84 (s, 1H, O═C—H), 6.26 (1H, s, OH), 5.20 (s, 2H, CH2Ph).

Provenance & Evidence