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nic

In this reaction, I don't know how I could place a methyl in the benzyl carbon. My first idea was to treat the compound with OsO4/H2O2 to form the vicinal diol, and then dehydrate in acidic medium and heat, but in this way I assume that carbocation is formed in the most substituted carbon, so I suppose that it should form in the other carbon and transpose a methyl, then with an oxidation get the carbonyl in the desired position, but this is It contradicts my idea of ​​the formation of carbocation in the most substituted carbon. Any other idea?

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    $\begingroup$ You are on the right track. With acid it is a pinacol rearrangement initiated by forming the benzyl carbocation. THere will be no need for an oxidation after the methyl migration. Just lose a proton from the oxygen. $\endgroup$
    – user55119
    Commented Jan 19, 2020 at 3:22
  • $\begingroup$ You're absolutely right, I hadn't taken into account the great stability of the carbocation in a benzyl position. Thank you $\endgroup$
    – Arnau
    Commented Jan 19, 2020 at 3:37

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