Acetonitrile → 3-Acetoxycyclohexene

Temperature

0 °C

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.

1. customAfter removing the residual copper powder
2. filtrationby filtration
3. washThe organic layer was successively washed with a 2N aqueous hydrochloric acid solution, water
4. dry with materialan aqueous solution saturated with sodium hydrogen carbonate and an aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate
5. customAfter evaporating the solvent
6. distillationthe residue was distilled under reduced pressure

ORD record

ord-d9b07567e0b546bbb9c7e1ae86c4adbe

Source dataset

uspto-grants-1978_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04069385