Hydrochloric Acid → Methyl 11-mercaptoundecanoate

Participants

Reaction Steps

Compound 104 (15.6 g, 56.9 mmol) in methanol (50 ml) was added to a solution of hydrogen chloride in methanol (HCl was bubbled into 600 ml of MeOH for 10 min). The reaction was monitored by TLC (SiO2, ethyl acetate:isooctane 1:5). After 48 h, an excess of sodium hydrogen carbonate was added and the mixture was diluted with dichloromethane (150 ml), filtered and concentrated. Distillation gave pure 105 (9.0 g, 68%) with b.p. 93°-94° (7×10-2 torr). 1H-NMR (CDCl3, Me4Si) δ 3.68 (s, 3H, MeO), 2.53 (q, 2H, J~7 Hz, H--S--CH2), 2.31 (t, 2H, J=7.5 Hz, CH2CO). 13C-NMR (CDCl3, Me4Si) δ 174.2 (CO), 51.3, 34.0, 33.9, 29.3, 29.2, 29.1, 29.0, 28.9, 28.3, 24.8, 24.5.

Provenance & Evidence