Methanol → Methyl 2-methoxy-5-methylthiobenzoate

Participants

Reaction Steps

Combine 2-methoxy-5-methylthiobenzoic acid (6.82 g, 34.4 mmol) and methanol (65 mL). Cool in an ice bath. Add slowly dropwise thionyl chloride (2.8 mL, 38 mmol). Warm to ambient temperature. After 18 hours, evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 25% hexane/dichloromethane to give methyl 2-methoxy-5-methylthiobenzoate, Rf=0.06 (silica gel, 65% hexane/dichloromethane).

Provenance & Evidence