Methanol → Methyl 3-hydroxy-5-methoxybenzoate

Participants

Reaction Steps

To a stirred solution of methyl 3,5-dihydroxybenzoate (80 g, 0.52 mol) in CH3OH (600 ml), was added concentrated H2SO4 (40 ml) in portions at room temperature. The reaction mixture was heated to reflux temperature for 4 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate. This solution was washed with a saturated aqueous Na2CO3 solution, brine, dried over Na2SO4 and concentrated under reduced pressure to give methyl 3-hydroxy-5-methoxybenzoate (73 g) as a white solid. The crude product was used in the next step without further purification.

Provenance & Evidence