Thioglycolic Acid → 2-benzoylsulfanylacetic Acid

Participants

Reaction Conditions

Reaction Steps

In advance, succinimidyl-S-benzoylmercaptoacetic acid (BMS) was synthesized as follows. Two-layer system of toluene (75 mL) and water (75 mL) was cooled in an ice-water bath, sodium hydroxide (8.86 g, 221.5 mmol) was added thereto. Next, mercaptoacetic acid (9.22 g, 100 mmol) was added dropwise and washed with 5 mL of water. Further, benzoyl chloride (14.61 g, 100.3 mmol) was added dropwise, and washed with 5 mL of toluene. The reaction was conducted with stirring at about 5° C. for 30 minutes, then at room temperature for 3.5 hours. The reaction mixture was subjected to separation, the organic layer was extracted in 3 times with 10 mL of water, and the aqueous layers were combined together. Under stirring, 12 mL of concentrated hydrochloric acid was added dropwise to the aqueous layer to adjust pH 1-2, and the crystals formed were collected by filtration. The crystals were dried in a desiccator, then washed with hexane, and dissolved in ethyl acetate. The solvent was distilled away to give S-benzoylmercaptoacetic acid (19.19 g, 97.8 mmol, 98% yield) as colorless needle-like crystals.

Provenance & Evidence