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Nuclear methylation of β-resorcylic aldehyde

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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.

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Authors and Affiliations

  1. Department of Chemistry, Andhra University, Waltair

    T. R. Seshadri & V. Venkateswarlu

Authors
  1. T. R. Seshadri
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  2. V. Venkateswarlu
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Seshadri, T.R., Venkateswarlu, V. Nuclear methylation of β-resorcylic aldehyde. Proc. Indian Acad. Sci. (Math. Sci.) 14, 297–306 (1941). https://doi.org/10.1007/BF03046071

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  • DOI: https://doi.org/10.1007/BF03046071

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