Nuclear methylation of resacetophenone - Preparation of 3-methylresacetophenone and its derivatives
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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.