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Issue 0, 1971
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3-Hydroxy-3-methyl-1,1-dimethoxybutane, a new reagent for dimethylchromenylation: synthesis of lonchocarpin, jacareubin, evodionol methyl ether, and other chromens

Abstract

Like citral, 3-methylbut-2-enal condenses under pyridine catalysis with suitable meta-dihydric phenols to give chromens having the 2,2-dimethyl-substitution pattern common in Nature. Citral acetal and 3-methyl-1,1-dimethoxybut-2-ene can replace the free aldehydes, and this observation has led to the development of 3-hydroxy-3-methyl-1,1-dimethoxybutane as a stable and readily accessible dimethylchromenylation reagent. Synthesis of various dimethylchromens, among them lonchocarpin, jacareubin, and evodionol methyl ether, illustrate its use. But-2-enal and cinnamaldehyde may be used in chromenylation reactions.

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Article type: Paper
DOI: 10.1039/J39710000811
J. Chem. Soc. C, 1971, 811-816

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    3-Hydroxy-3-methyl-1,1-dimethoxybutane, a new reagent for dimethylchromenylation: synthesis of lonchocarpin, jacareubin, evodionol methyl ether, and other chromens

    W. M. Bandaranayake, L. Crombie and D. A. Whiting, J. Chem. Soc. C, 1971, 811
    DOI: 10.1039/J39710000811

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