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providence14

2,2-dimethylcyclohexanone to 2,3-dimethylphenol

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Hey Everyone,

 

Anyone out there have any idea on the mechanism for reacting 2,2-dimethylcyclohexanone with H2SO4 to yield 2,3-dimethylphenol.

 

Once you protonate the ketone and form a benzene ring, how the heck is the methyl moved down to the 3 position? post-42771-0-67032700-1301377364_thumb.jpg

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Try protonating one of the double bonds to start. It's not an aromatic system (yet) so this is a reasonable starting place.

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