Abstract
Methyl 2-hydroxy-4-methoxy-6-phenylbenzoate (3b) was synthesized by treatment of methyl 6-phenyl-β-resorcylate (3a) with diazomethane. 5-Phenylresorcinol (8) was carboxylated in a Kolbe–Schmitt reaction to give γ-resorcylic acid 7b. Treatment of 7b with diazomethane gave a mixture of the corresponding dihydroxy ester 7c, monomethoxy ester 7a, and dimethoxy ester 7d. Evidence is presented that the structure of a compound obtained by Douglas and Money from base treatment of phenyl dipyrone 1 is 7a rather than the previously assigned 3b. A mechanistic proposal is presented.
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