T. T. Howarth, T. Harris
Dec 1, 1968
Citations
0
Influential Citations
3
Citations
Journal
Canadian Journal of Chemistry
Abstract
Methyl 2-hydroxy-4-methoxy-6-phenylbenzoate (3b) was synthesized by treatment of methyl 6-phenyl0-resorcylate (3a) with diazomethane. 5-Phenylresorcinol (8) was carboxylated in a Kolbe-Schmitt reaction to give y-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 36. A mechanistic proposal is presented. Canadian Journal of Chemistry. 46, 3739 (1968)