Hydrochloric Acid → Methyl 4-methoxy-3-propyl-5-sulfanylbenzoate

Participants

Reaction Steps

To a stirred solution of 3-ethoxythiocarbonylthio-4-methoxy-5-propylbenzoic acid methyl ester (720 mg, 2.20 mmol) in THF (13 mL) at room temperature was added MeONa (0.5 M in MeOH, 13 mL, 6.5 mmol, 3 eq.). The reaction mixture was refluxed for 75 min, then cooled to room temperature and added to 1 N HCl aqueous solution (100 mL). The resulting mixture was extracted with EtOAc/hexanes (1:1, 100 mL). The organic layer was washed with brine (50 mL), dried over MgSO4 and concentrated in vacuo to give 3-mercapto-4-methoxy-5-propylbenzoic acid methyl ester (0.55 g). The product was used without further purification.

Provenance & Evidence