Benzyl Bromide → 4-Benzyloxy-3-hydroxybenzaldehyde

Participants

Reaction Steps

A mixture of 3,4-dihydroxybenzaldehyde (1.38 g, 10 mmol), benzyl bromide (1.71 g, 10 mmol), and K2CO3 (1.24 g, 9 mmol) in 20 mL acetone was stirred at rt for 15 h under Ar atmosphere. Solid was filtered off and the filtrated was diluted with EtOAc (100 mL) and washed with NaH2PO4 (sat. 100 mL), and dried over MgSO4 and concentrated. The residue was chromatographed (hexane/EtOAc) to afford 4-(benzyloxy)-3-hydroxybenzaldehyde as a white solid (1.15 g, 50%). 1H NMR (400 MHz, CDCl3) δ 9.84 (s, 1H), 7.46 (d, J=2.0 Hz, 1H), 7.44-7.40 (m, 6H), 7.04 (d, J=8.0 Hz, 1H), 5.80 (s, 1H), 5.21 (s, 2H); MS (ESI) m/z 229 (M+H+).

Provenance & Evidence