Methanol → Methyl 2-hydroxy-4-(methylthio)benzoate

Participants

Reaction Conditions

Reaction Steps

The 2-hydroxy-4-(methylthio)benzoic acid (836 mg, 4.54 mmol) was dissolved in MeOH (45 mL). Thionyl chloride (0.35 mL, 4.80 mmol) was added and the solution was heated to 65° C. and left overnight. TLC indicated that there was still starting material present; so more thionyl chloride (1.0 mL, 13.7 mmol) was added. After about 1.5 hour, TLC indicated formation of baseline material; so the reaction was concentrated in vacuo. The crude residue was purified using flash column chromatography (100% CH2Cl2) to give the desired compound as an off-white solid (567 mg, 2.86 mmol, 63%).

Provenance & Evidence