Benzene → Allyl 11-mercaptoundecanoate

Participants

Reaction Steps

1.09 g (5 mmol) 11-mercaptoundecanoic acid was placed along with 3 g (51.7 mmol) allyl alcohol, 0.57 g p-toluenesulfonic acid and 40 ml benzene in a round bottom flask and heated for 25 minutes with azeotropic removal of water using a Dean-Stark apparatus. The reaction mixture was then cooled and washed with 10% aqueous sodium bicarbonate solution (3×20 ml). The benzene layer was dried over anhydrous MgSO4, and removal of solvent yielded a colorless oil (0.997 g, 77%). 1H-NMR (300 MHz, CDCl3) 1.27, m, 12 H; 1.60, m, 5 H; 2.33, t, 2 H, J=7.5 Hz; 2.51, q, 2 H, J=7.4 Hz; 4.59, dt, 2 H, J=5.7, 1.4 Hz; 5.20-5.39, m, 2 H; 5.85-6.00, m, 1 H; IR (film) 2560 (SH), 1730 (C=O), 1640 cm-1 (C=C); EI-MS; 258 (M+).

Provenance & Evidence