Acetonitrile → 3-Acetoxycyclohexene

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.631 g of (S)-(-)-N-salicylidene-1-phenyl-2-(p-tolyl)ethylamine, 0.182 g of cupric acetate, 0.70 g of copper powder, 15 ml of acetonitrile, 10 ml of ethyl acetate, 5 ml of acetic acid, 15 ml of cyclohexene and 5 ml of t-butyl peroxybenzoate was stirred at 0° C for 24 hours in a nitrogen atmosphere. After removing the residual copper powder by filtration, the filtrate was admixed with 50 ml of benzene. The organic layer was successively washed with a 2N aqueous hydrochloric acid solution, water, an aqueous solution saturated with sodium hydrogen carbonate and an aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was distilled under reduced pressure to obtain 1.90 g or 2-cyclohexenyl acetate. B.P. 75°-76° C/21 mmHg.

Provenance & Evidence