Sulfuric Acid → 11-Mercaptoundecanoic Acid

Participants

Reaction Steps

4 g (15.09 mmol) 11-bromoundecanoic acid is added along with 1.505 g thiourea (19.82 mmol) and 15 ml water to a round botton flask, and the mixture is refluxed for 3 hours. 10.2 ml 3M sodium hydroxide (30.6 mmol) was then added and the mixture was refluxed for one additional hour. The reaction mixture was cooled in an ice bath, and dilute sulfuric acid was added dropwise until the solution had a pH of about 2. The cloudy solution was then extracted with ether (2×25 ml), dried over anhydrous MgSO4, and concentrated under reduced pressure to give a white solid (3.1 g, 94%). 1H-NMR (300 MHz, CDCl3) 1.28, m, 10 H; 1.60, m, 7 H; 2.35, t, 2 H, J=7.3 Hz; 2.50, q, 2 H, J =7.5 Hz.

Provenance & Evidence