4-Hydroxybenzaldehyde → Benzaldehyde, 4-(phenylmethoxy)-

Participants

Reaction Steps

A mixture of 4-hydroxybenzaldehyde (12.2 g, 100 mmol), benzyl bromide (25.66 g, 150 mmol), and cesium carbonate (97.8 g, 300 mmol) in DMSO (200 mL) under nitrogen at room temperature was stirred overnight. The reaction was filtered to remove the solids, and then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel eluting ethyl acetate:hexane (15:85, v:v) to give 4-benzyloxy-benzaldehyde (18.72 g, 80%) as a glass. MS found: (M+H)+=213.

Provenance & Evidence