Thioglycolic Acid → HCID 178526169, compound

Participants

Reaction Steps

To a solution of 3-bromobenzyl bromide (23.75 g, 90 mmol) and thioglycolic acid (11.42 g, 120 mmol) in ethanol (150 mL) was added potassium hydroxide (14.24 g, 250 mmol) in water (50 mL). The reaction was heated at reflux for 3.5 h, cooled and the ethanol was evaporated. The residue was quenched with water (100 mL) and the mixture was extracted with ether (50 mL). The aqueous layer was acidified to pH 1 with concentrated hydrochloric acid, extracted with ethyl acetate (2×100 mL) and the organic phase was dried. Evaporation of the solvent followed by washing of the residue with hexane afforded 3-bromophenylmethylthioacetic acid as a white solid (92%), mp 90°-91° C.: 1H NMR (CDCl3) δ 3.10 (s, 2H), 3.82 (s, 2H), 7.20-7.29 (m, 2H), 7.39-7.42 (dd, 1H), 7.52 (dr 1H); IR (KBr) 1706 cm-1 ; Mass spectrum m/z 280 (M+NH4); Anal. calcd. for C9H9O2SBr: C 41.39, H 3.47, S 12.28; Found C 41.43, H 3.49, S 12.10.

Provenance & Evidence