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 4‐ethyl‐1,1‐dimethyl‐3,4‐dihydro‐2H‐naphthalene

Benzylic hydrogen is required for the side chain oxidation of benzene. But for this compound the top branch connected to the benzene ring does not have a benzylic hydrogen. So, will the top branch be broken off in the process of oxidation?

The reagents and conditions for the side chain oxidation are $\ce{KMnO4}$ with $\ce{H2SO4}$ and heat.

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  • $\begingroup$ I am not 100% sure but the products should be ester combinations of phthalic acid, succinic acid and ethanoic acid. $\endgroup$ Commented May 28, 2021 at 5:20
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    $\begingroup$ I think the benzylic dimethyl group will be resistant to oxidation and you'll end up with a dimethylphenylacetic acid there. The other site will be oxidised up to the benzoic acid. $\endgroup$
    – Waylander
    Commented May 28, 2021 at 8:23
  • $\begingroup$ This is best settled in the lab. My guess is ketones then benzoate at the tertiary carbon then destruction of the benzene ring. An interesting reaction might be with peroxide to give a phenol and ketone. Why destroy such an intriguing compound? $\endgroup$
    – jimchmst
    Commented Aug 27, 2023 at 5:48

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