Benzyl Bromide → 3-Benzyloxy-4-methylbenzoic acid benzyl ester

Participants

Reaction Steps

To a solution of 3-hydroxy-4-methylbenzoic acid (5.0 g) in N,N-dimethylformamide (100 mL) were added cesium carbonate (32 g) and benzyl bromide (12 g) at the same temperature and this mixture was stirred at room temperature for 2 days. To this reaction mixture was added a saturated aqueous sodium bicarbonate solution and this mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and this residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (7.5 g).

Provenance & Evidence