Benzyl Bromide → 2-(Benzyloxy)-3,4-dimethoxybenzaldehyde

Participants

Reaction Steps

Benzyl bromide (12.9 ml, 0.108 mol) was added to a suspension of 2-hydroxy-3,4-dimethoxybenzaldehyde (19 g, 0.104 mol) and potassium carbonate (14.41 g, 0.104 mol) in acetone (200 ml) and the reaction stirred at reflux for 3 hours. On cooling, the mixture was concentrated under reduced pressure and the residue partitioned between water (150 ml) and dichloromethane (150 ml). The organic layer was filtered through silica, washing through with hexane and then ethyl acetate. Evaporation of the filtrate under reduced pressure gave a yellow gum. The crude product was purified on silica gel eluting with ethyl acetate:hexane (30:70 v/v) to give the subtitle compound (25.9 g, 88%). Rf 0.82 (ethyl acetate:hexane 1:1, v/v). MS m/z 273 (MH)+.

Provenance & Evidence