Hydrochloric Acid → Methyl 3,4-dimethoxy-5-sulfanylbenzoate

Participants

Reaction Steps

To a stirred solution 3-dimethylcarbamoylthio-4,5-dimethoxybenzoic acid methyl ester (800 mg, 2.67 mmol) in THF (21 mL) was added MeONa (0.5 M in MeOH, 21 mL) at room temperature and the reaction was heated to reflux. After refluxing for 3 h, the reaction mixture was cooled to room temperature, poured into 1 N HCl aqueous solution (150 mL) and extracted with mixture of EtOAc:hexane (1:1, 150 mL). The organic layer was washed with brine (100 mL), dried over MgSO4 and concentrated in vacuo to give 3-mercapto-4,5-dimethoxybenzoic acid methyl ester (0.581 g).

Provenance & Evidence