Benz But Doesn’t Break. Part V

The third step of the modified benzilic acid synthesis project proceeded well under the same conditions as the benzil to benzilic acid rearrangement as outlined in a previous post. The products were characterized by melting point, UV absorption, IR, 1H and 13C NMR. The carboxylic acid products were not compatible with the GC column we were using. An interesting phenomenon was observed in the IR. Apparently, the alcohol group of (dimethyl)benzilic acid gives and uncharacteristically sharp peak at 3399 cm-1 which is also observed with (dimethyl)benzoin.
DMBenzil2DMBenzilicacid
DMBezilicAcid_IR

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