Nuclear methylation of resacetophenone: preparation of 3-methylresacetophenone and its derivatives

Abstract

The methylation of resacetophenone and its ω-methoxy derivative using methyl iodide and methyl alcoholic potash has been studied. The former gave 2-hydroxy-3-methyl-4-methoxyacetophenone the constitution of which was established by demethylation to 3-methylresacetophenone and comparison with a specimen prepared from 2-methylresorcinol. In the same way ω-methoxyresacetophenone gave 2-hydroxy-3-methyl-ω:4-dimethoxyacetophenone which was subsequently converted to 3:7-dimethoxy-8-methylflavone. The identity of this flavone was proved by its synthesis from 2-methyl-resorcinol. It is concluded that under the above conditions resacetophenone undergoes nuclear methylation in the 3-position and that the hydroxyl group in the 4th position gets etherified.