Acetyl chloride → HCID 22421025, compound

Participants

Reaction Steps

Di-isopropylamine (44.7 ml.) was dissolved in dry tetrahydrofuran (400 ml.) and cooled to -78° under nitrogen with mechanical stirring. A solution of n-butyllithium in hexane (1.6M, 197 ml.) was added. After stirring at -78° for 10 minutes a solution of dimethyl cyclohexane-1,4-dicarboxylate ((52.6 g.) Lancaster) in tetrahydrofuran (200 ml.) was added. After stirring for a further 30 minutes at -78° a solution of acetyl chloride (22.5 ml.) in tetrahydrofuran (200 ml.) was added. The reaction mixture was allowed to warm up to room temperature over a period of 3 hours. Water was then added and the mixture extracted with ether. The ethereal extracts were washed with water, saturated sodium bicarbonate solution, dilute hydrochloric acid and brine, and were then dried over anhydrous magnesium sulphate. Evaporation under reduced pressure gave a colourless oil which was slowly distilled to yield dimethyl 1-acetylcyclohexane-1,4-dicarboxylate (23.3 g, b.p. 114°-120°/0.4 mmHg). Nuclear Magnetic Resonance spectrum (NMR) was as follows: 3.89, 3H, s; 3.75, 3H, s; 2.6-1.4, 13H, m.

Provenance & Evidence