Hydrochloric Acid → Oleyl acetate

Participants

Reaction Steps

a solution of 2.8 g of acetyl chloride in 10 ml of dry benzene was added dropwise, with stirring, to an ice-cold solution of compound III (5.0 g) and 2.8 g of pyridine in 20 ml of dry benzene. Following addition, stirring was maintained at room temperature for 30 minutes and the mixture was then refluxed for 2 hours. The cooled mixture was diluted with 30 ml of ether and treated with sufficient cold 5% HCl to make the mixture strongly acid. The layers were separated and the aqueous layer was shaken once with 20 ml of ether; the combined organic layers were washed with three 10-ml portions of cold H2O and dried over Na2SO4. Evaporation of the solvent and distillation of the residue gave 5.1 g (85%) of compound IV as a colorless liquid boiling at 139°-143° (0.1 mm), nD25 1.4493.

Provenance & Evidence