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Topic: Dealkylation  (Read 6366 times)

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Offline poorstudent83

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Dealkylation
« on: September 04, 2009, 03:02:49 PM »
Hi!!

I'm looking for a mechanism for the dealkylation of aromatic compounds. For example, the cleavage of the tert-butyl group from p-tert-butylphenol using phenol/AlCl3/toluene. I think I understand that the phenol "accepts" the tert-butyl group. Is the toluene also playing a role besides being a solvent??
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Offline poorstudent83

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Re: Dealkylation
« Reply #1 on: September 05, 2009, 10:51:24 AM »
Ok, after much searching I've come to realise it's a reverse Friedel-Crafts alkylation reaction. Any ideas on the mechanism?!
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Re: Dealkylation
« Reply #2 on: December 10, 2009, 11:03:09 AM »
So far im aware its called a F-C Dealkylation rxn  :P    But toluene will undergo a disproportionation rxn to form benzene and xylene. The mechanism involves a lewis acid catalyst (AlX3) and is detailed in March's Advanced Organic Chemistry (6th ed) pg742-44
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