Hydrochloric Acid → Methyl 3-methoxy-5-sulfanylbenzoate

Participants

Reaction Steps

To a stirred solution of 3-dimethylcarbamylthio-5-methoxybenzoic acid methyl ester (500 mg, 1.86 mmol) in THF (10 mL) at room temperature was added MeONa (0.5 M in MeOH, 10.0 mL, 5.0 mmol, 2.69 eq.). The reaction was refluxed for 2 h, then cooled to room temperature and added to 1.0 N HCl aqueous solution (150 mL). The resulting mixture was extracted with EtOAc/hexanes (1:1, 150 mL). The organic layer was washed with brine (100 mL), dried over MgSO4 and concentrated in vacuo to give 3-mercapto-5-methoxybenzoic acid methyl ester (0.365 g). The product was used without further purification.

Provenance & Evidence