2-Mercaptophenylacetic acid → 2-[2-(Methyldisulfanyl)phenyl]acetic acid

Participants

Reaction Steps

To a solution of (2-mercaptophenyl)acetic acid (449 mg) in H2O (15 mL) and ethanol (7 mL) was added methyl methanethiosulfonate (372 mg, 2.93 mmol). After stirring for 20 hours, the reaction mixture was diluted with ether and washed with 1 N KOH twice. The water layers were combined and acidified to pH 2 with 5 N hydrochloric acid. This solution was extracted with CH2Cl2 three times. The organic layers were combined, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford 576 mg (100% yield) of the (2-methyl disulfanylphenyl)acetic acid product in the form of a yellow oil: 1H NMR (400 MHz, CDCl3) δ (ppm): 2.42 (s, 3H), 3.92 (s, 2H), 7.10-7.40 (m, 3H), 7.80 (d, J=7.6 Hz, 1H), 10.34 (s, 1H); 13C NMR (100 MHz, CDCl3) δ (ppm): 22.7, 38.9, 127.8, 128.1, 128.3, 128.8, 130.4, 130.8, 130.9, 177.1. HRMS (EI): m/e calcd. for C9H10O2S2: 214.012223, Found: 214.012637 (Δ=−1.9 ppm).

Provenance & Evidence