Acetonitrile → 3-Acetoxycyclohexene

A mixture of 0.6 g of di-L-prolinato Copper (II), 0.7 g of copper powder, 15 ml of acetonitrile, 5 ml of acetic acid, 15 ml of cyclohexene and 5 ml of t-butyl peroxybenzoate was stirred at 20° to 25° C for 3 hours in a nitrogen atmosphere. After it was confirmed on TLC (thin layer chromatography) that the residual t-butyl peroxybenzoate was no longer present, the remaining copper powder was filtered off and the filtrate was admixed with 50 ml of benzene. The organic layer was successively washed with a 2N hydrochloric acid, an aqueous solution saturated with sodium chloride, an aqueous solution saturated with sodium hydrogen carbonate and an aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate. After removing the solvent, the residue was distilled under reduced pressure to obtain 1.40 g of 2-cyclohexenyl acetate. B.P. 75°-76° C/21 mmHg.

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

ORD record

ord-4b092d9fd5904f69ab8476614b513e62

Source dataset

uspto-grants-1978_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04069385