Hydrochloric Acid → Methyl 3-hydroxy-5-methoxybenzoate

Participants

Reaction Steps

To a solution of methyl 3,5-dihydroxybenzoate (28.0 g) in DMF (300 mL) was added 60% sodium hydride (4.70 g) at 0° C., and the mixture was stirred for 30 min. Iodomethane (23.7 g) was added dropwise, and the mixture was stirred at 0° C. for 1 hr. 1N Hydrochloric acid (300 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (10.1 g) as a white solid.

Provenance & Evidence