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Author: Subject: Chlorination of benzilic acid

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[*] posted on 26-4-2011 at 03:41
Chlorination of benzilic acid


Is it possible to chlorinate benzilic acid to diphenylchloroacetic acid (2-chloro-2,2-diphenylacetic acid) with hydrochloric acid? It is a substituted benzyl alcohol, and at least benzyl alcohol can be chlorinated to benzyl chloride with hydrochloric acid.

I have searched beilstein for references but only found two for chlorinating it with POCl3 and SOCl2 (Ber 36: 145 and Ber. 43: 2471).

I also found a reference that mentions the ethyl ester of diphenylchloroacetic acid is produced when benzilic acid is heated with HCl/ethanol (Ber. 22: 1213). So if that is possible shouldn't diphenylchloroacetic acid itself be produced with just hydrochloric acid?
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