Abstract
Oxidation of 6-methyl-2-phenylbenzofuran with chromium trioxide in acetic acid gave an unusual dimeric oxidation product, 2, 2'-dibenzoyloxy-4, 4'-dimethylbenzil (II). Structural establishment came from several chemical evidences including an interesting acyl migration from 2, 2'-dibenzoyloxy-4, 4'-dimethylhydrobenzoin (III) to 2, 2'-dimethoxy-4, 4'-dimethylhydrobenzoin dibenzoate (IV) during methylation with diazomethane.
On the other hand, oxidation of the same benzofuran with Jones' reagent afforded 2-hydroxy-4-methylbenzil (IX). Furthermore, on treatment with chromium trioxide. pyridine complex, the material (II) was recovered quantitatively.
