Potassium Carbonate → 3-(mercaptomethyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

Into a 500-mL round bottom flask, was placed a solution of 3-(acetylthiomethyl)benzoic acid (16.4 g, 78.10 mmol, 1.00 equiv) in methanol (150 mL), and a solution of potassium carbonate (26.9 g, 194.93 mmol, 2.50 equiv) in water (70 mL). The resulting solution was stirred for 4 h at 60° C. The resulting mixture was concentrated under vacuum, diluted with 200 mL of water, and then adjusted to pH 3 with 10% hydrochloric acid. The mixture was extracted with 3× (100/20 mL) of ethyl acetate/tetrahydrofuran and the organic layers combined, washed with 1×100 mL of brine, then dried over sodium sulfate and concentrated under vacuum. This resulted in 12 g (91%) of 3-(mercaptomethyl)benzoic acid as a brown solid.

Provenance & Evidence