Methanol → Methyl 2-(3-mercaptophenyl)acetate

Participants

Reaction Steps

2-(3-Mercaptophenyl)acetic acid (1.0 g, 6.0 mmol) was dissolved in dry methanol (40 mL). To this solution 10 drops concentrated sulfuric acid was added and the reaction mixture was heated to reflux for 36 hours. The reaction mixture was then concentrated to about half the volume, diluted with ethyl acetate, and the organic layer washed with saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate and concentrated to afford methyl 2-(3-mercaptophenyl)acetate as an oil (0.55 g, 3.0 mmol, 50% yield). 1H NMR (CDCl3) 7.05 ppm, 3H, m; 6.88 ppm, 1H, m; 3.53 ppm, 3H, s; 3.38 ppm, 2H, s.

Provenance & Evidence