Hydrochloric Acid → Benzoic acid, 3-mercapto-

Participants

Reaction Steps

To a suspension of 3-(chlorosulfonyl)benzoic acid (22.0 g, 0.10 mol) and zinc powder (87.5 g, 1.3 mol) in benzene (150 mL) was added at 0° C., in a dropwise manner, concentrated hydrochloric acid (150 mL, 10 M). The mixture was heated at reflux, stirred for 1 hour, cooled to room temperature, and filtered through a pad of celite, which was subsequently washed with benzene (3×50 mL). The organic layer was separated and washed with water (100 mL), and brine (100 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a white solid which was recrystallised from aqueous ethanol (9.5 g, 62%) to give the title compound as a solid, mp 147° C.

Provenance & Evidence