The Oxidation of ( + )-p-Menth-3-ene with Selenium Dioxide

The oxidation of ( + )-p-menth-3-ene by selenium dioxide in a mixture of glacial acetic acid and acetic anhydride was examined with special attention paid to the position of the oxidative attack, i. e., the C2− or C5-position of the hydrocarbon. Careful examination of the reaction product showed that this oxidation yielded only (±)-p-menth-3-en-5-yl acetate (major product), (±)-p-menth-3-en-5-ol and (±)-p-menth-3-en-5-one. Thus, this oxidant selectively attacks an active methylene group at the C5-position of p-menth-3-ene.