Hydrochloric Acid → HCID 178467885, compound

Participants

Reaction Steps

A solution of trans-(4-t-butylcyclohexyl)acetic acid (9.96 g) in dry DME (30 ml) was added over 10 min to a vigorously stirred suspension of powdered lithium hydride (0.5 g) in dry DME (30 ml). The mixture was refluxed for 2.5 hr, cooled on ice and a solution of methyl lithium in ether (63 ml; 1.6M solution) added over 30 min. The mixture was then stirred at room temperature for 2 hr, and poured into a mixture of conc. hydrochloric acid (13.5 ml) and water (200 ml). The organic phase was separated and the residue extracted with ether. The extracts were combined, washed with aq. sodium carbonate and satd. brine, dried over magnesium sulphate and concentrated in vacuo. Distillation afforded the title compound (7.7 g), b.p. 90°-100°/0.3 mm, NMR δH (CDCl3) 2.28 (2H, d, J 7Hz), 2.12 (3H, s), 1.85-1.65 (6H, m), 1.05-0.85 (4H, m), 0.85 (9H, s).

Provenance & Evidence