Benzylic Oxidation of Cyclic Molecules Using KMnO₄ What is the product of the permanganate oxidation of 1-methylindane (1-methyl-2,3-dihydro-1⁠H-indene)?



There are two choices of benzylic protons (one proton on the carbon with the methyl group at the top of the cyclopentane, and two protons on the carbon in the cyclopentane at the bottom of the molecule).

I figure that the ketone is added to the carbon that has two benzylic protons, and that the other carbon with a benzylic proton is untouched. Am I correct?
For the homogenous permanganate oxidation of aromatic side chains, as long as there is at least one benzylic hydrogen, then the side chain will be oxidized to the corresponding benzoic acid.  Here are some examples.



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Look at the third example, the permanganate oxidation of tetralin to phthalic acid.  It is very analogous to your molecule.  Your molecule would also be oxidized to phthalic acid.