Methanol → Methyl 3-hydroxy-2-methylbenzoate

Participants

Reaction Steps

To a methanol solution (25 mL) at 0° C. was dropwise added thionyl chloride (9.6 mL, 0.13 mol). After 15 minutes, 3-hydroxy-2-methylbenzoic acid (4 g, 0.033 mol) was added and the resulting mixture was stirred at room temperature for 24 hours. Volatile was removed under vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was separated, washed with water and saturated sodium chloride solution, and was dried over sodium sulfate. After concentration, the crude product was recrystallized from dichloromethane and hexane to gave 3.48 g of methyl 3-hydroxy-2-methylbenzoate.

Provenance & Evidence