Hydrochloric Acid → Ethyl cyclohexanoate

Participants

Reaction Steps

To a solution of ethanol (45 ml) and triethylamine (78 g) in toluene (120 ml), cyclohexane carbonyl chloride (75 g, 0.51 mol) was added dropwise at 15° C. or lower, and stirring was continued for 3 h at room temperature. The reaction mixture was poured into cold H2O (350 ml), acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic extract was washed thrice with H2O (150 ml), dried over anhydrous Na2SO4 and the solvent was removed in vacuo. The residue (93 g) was distilled under reduced pressure to give the title compound as a colorless oil; yield: 64 g; bp 101°-102° C./35 mmHg (Lit: bp 194° C./~760 torr: G. A. Olah, T. Keumi, D. Meider, Synthesis, 1978, 929.).

Provenance & Evidence