Benzyl Bromide → Methyl 3-(benzyloxy)-5-hydroxybenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3,5-dihydroxybenzoate (8.41 g, 50.0 mmol) and benzyl bromide (3.57 mL, 30.0 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (4.15 g, 30.0 mmol), and the mixture was stirred under a nitrogen atmosphere at 70° C. for 16 hr. The reaction mixture was concentrated under reduced pressure, and water was added. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-30% ethyl acetate/hexane) and recrystallized from ethyl acetate-hexane to give the title compound (3.56 g, yield 46%) as colorless prism crystals.

Provenance & Evidence