Nuclear methylation of resacetophenone

Preparation of 3-methylresacetophenone and its derivatives
  • S. Rangaswami
  • T. R. Seshadri


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.


Flavone Methyl Iodide Sodium Benzoate Anhydrous Potassium Carbonate Phenone 
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Copyright information

© Indian Academy of Sciences 1938

Authors and Affiliations

  • S. Rangaswami
    • 1
  • T. R. Seshadri
    • 1
  1. 1.Department of ChemistryAndhra UniversityWaltair

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