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Nuclear methylation of β-resorcylic aldehyde

  • T. R. Seshadri
  • V. Venkateswarlu
Article
  • 21 Downloads

Summary

A survey of past work on the nuclear methylation and ethylation of resorcinol and phloroglucinol derivatives is given and a mechanism for this reaction suggested. The nuclear methylation of β-resorcylic aldehyde has now been carried out giving rise to a good yield of the product (A). Its constitution as 4-methoxy-3-methyl-2-hydroxy benzaldehyde has been established in two ways: (i) A sample of 4-methoxy-3-methyl-2-hydroxy benzaldehyde was prepared according to the synthetic method of Jones and Robertson and compared with (A). (ii) The corresponding coumarin was prepared from (A) and was identified as 7-methoxy-8-methyl coumarin by comparison with the compound obtained by independent synthesis, starting from 2-methyl-resorcinol and passing through 7-hydroxy-8-methyl-coumarin as an intermediate stage. The same coumarin was also prepared by the reduction of umbelliferone-8-aldehyde and subsequent methylation.

Keywords

Coumarin Resorcinol Potassium Carbonate Methyl Iodide Diethyl Malonate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Indian Academy of Sciences 1941

Authors and Affiliations

  • T. R. Seshadri
    • 1
  • V. Venkateswarlu
    • 1
  1. 1.Department of ChemistryAndhra UniversityWaltair

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