Acetic Acid → 3-Acetoxycyclohexene

Participants

Reaction Steps

In order to demonstrate that the 3,6-diacyloxycyclohexene can be prepared in a single step procedure, a mixture of 20.5 g. (0.25 moles) cyclohexene, 45 g. (0.75 moles) acetic acid and 45 g. of 90.5 weight percent purity tertiary butyl hydroperoxide (0.45 moles) and 0.4 g. cuprous chloride was heated at 80° - 85° C. for 10 hours at which time it was found that 97 weight percent of the hydroperoxide had been consumed. Analysis by glpc showed that 21 mole percent yield to 3-acetoxycyclohexene and a 25 mole percent yield to 3,6-diacetoxycyclohexene was obtained. The reaction mixture was treated as in Example I and the product distilled at 92° C. under 1 mm Hg pressure. Very little high boiling residue was found. It will be noted that although 0.5 moles of the hydroperoxide solution was used since it was not pure only 0.45 moles of the hydroperoxide itself was employed, i.e. slightly less than the desired 2:1 mole ratio of hydroperoxide to cyclohexene, a good yield of the diester was obtained.

Provenance & Evidence