Alcoholic potassium permanganate for oxidation

Question

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.

Possible duplicate of Oxidation of toluene to benzoic acid in presence of KMnO4 — ringo, Feb 20 '16 at 02:35
@ringo Not sure if this is a duplicate or not. Title and wording of the question refer to alcoholic $\ce{KMnO4}$, which is not what the linked question is about. Or, perhaps alcoholic is a typo in biogirl's blockquote? — hBy2Py, Feb 20 '16 at 03:11
@ringo I guess my question is a duplicate. I just went through the question but the answer given was not satisfactory. — biogirl, Feb 20 '16 at 06:22

score 2 · Answer 1 · edited Mar 08 '18 at 09:42

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.

Alcoholic potassium permanganate for oxidation

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