Acetone → Methyl 4-(allyloxy)benzoate

Participants

Reaction Steps

Anhydrous potassium carbonate (55 g) in acetone (400 ml) and allyl bromide (41.5 ml) were added to a stirred solution of methyl 4-hydroxybenzoate (60.8 g). The mixture was heated at reflux for 18 hours. The reaction mixture was cooled to ambient temperature, filtered and the residue washed with ethyl acetate. The filtrates and washings were combined, evaporated and the residue dissolved in dichloromethane. The organic phase was washed with 1M aqueous sodium hydroxide (2×75 ml), water, brine and dried (MgSO4). Evaporation gave methyl 4-allyloxybenzoate as an oil (76.4 g) which was used without further purification.

Provenance & Evidence