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

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      Permanent link:
      https://www.ias.ac.in/article/fulltext/seca/008/04/0214-0219

    • Keywords

       

      Flavone; Methyl Iodide; Sodium Benzoate; Anhydrous Potassium Carbonate; Phenone

    • 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.

    • Author Affiliations

       

      S Rangaswami1 T R Seshadri1

      1. Department of Chemistry, Andhra University, Waltair
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