Alcoholic potassium permanganate for oxidation A question in my textbook:


  Though alkaline and acidic $\ce{KMnO4}$ are both oxidizing agents, in the manufacture of benzoic acid from toluene, we only use alcoholic $\ce{KMnO4}$ as an oxidant. Why?


I am not able to figure out the answer. But I think maybe the acidic and alkaline $\ce{KMnO4}$ are too strong and may oxidize the benzene ring. Or the benzoic acid may react with the alkaline medium. (Though I wonder why it wouldn't react with alcohol to give ester)

I also tried digging around the web but couldn't come up with anything satisfactory.
Practical considerations, mainly that toluene is non-polar, inorganic. Aqueous $\ce{KMnO4}$ wouldn't be miscible so the oxidation can only take place in the interface. By using alcoholic $\ce{KMnO4}$, we can get the $\ce{KMnO4}$ into the organic layer much more easily, thus making the reaction much faster.

To form an ester, you generally need a dehydrating environment. Plus, the oxidation of toluene with $\ce{KMnO4}$ in neutral conditions will produce base which neutralizes the benzoic acid, thus deactivating it making it unable to undergo esterification.