Benzyl Bromide → 3-Benzyloxy-4-methoxybenzaldehyde

Participants

Reaction Steps

To a solution of 3-hydroxy-4-methoxybenzaldehyde (5.0 g, 33 mmol) in N,N-dimethylformamide (165 mL) is added benzyl bromide (4.3 mL, 36 mmol), followed by potassium carbonate (˜325 mesh, 14 g, 100 mmol). The reaction mixture is stirred for 4 hours at room temperature and then partitioned between diethyl ether and water. The aqueous phase is extracted with ether (3×50 mL). The combined ethereal extracts were washed twice with water and once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give 3-benzyloxy-4-methoxybenzaldehyde as golden oil, which crystallized upon standing to afford a white solid. The material is used in the following step without further purification.

Provenance & Evidence