Oxidation of diphenylmethanol to benzophenone

I'm looking for a reliable procedure for an undergraduate organic lab experiment: oxidation of diphenylmethanol to benzophenone.  I am updating our lab experiments and was thinking about introducing phase transfer catalysis, linked to a 2-step Grignard synthesis ( bromobenzene --> phenylmagnesium bromide  -->  diphenylmethanol  --> benzophenone).  I have found a JChem Ed paper that suggests using ethyl acetate, tetrabutylammonium hydrogensulfate and commercial bleach (hypochlorite).  The experiment looks promising, ( the article reports 70-85 % yield, after recrystallizing the product from hexane).  I'm curious to know if anyone does this experiment with their students and what their experience has been.


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James Hanson's picture
James Hanson | Sun, 09/28/2014 - 23:10

We have done this and it works.  If you want to add another step, photochemical reaction of banzophenone to benzpinacol is a good one.