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Long Chain Phenols. Part 17. The Synthesis of 5-resorcinol, 'Cardol monoene,' and of 5-resorcinol Dimethyl Ether, 'Cardol diene' Dimethyl Ether

DOI: 10.1039/P19810000132

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 132 - 141 (1981)

Update date:2022-08-05

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Authors:

Baylis, Christopher J.Baylis, Christopher J.

Odle, Stanley W.Odle, Stanley W.

Tyman, John H. P.Tyman, John H. P.

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Article abstract of DOI:10.1039/P19810000132

Two unsaturated compounds in the 'cardol' series, an important component phenol from Anacardium Occidentale, have been synthesised. 3,5-Dimethoxybenzaldehyde interacted with OH-protected 6-chlorohexan-1-ol in the presence of lithium to give, after acidic treatment, 1-(3,5-dimethoxyphenyl)heptane-1,7-diol which was hydrogenolysed selectively to 7-(3,5-dimethoxyphenyl)heptan-1-ol.Conversion into the bromide and alkylation of lithio-oct-1-yne gave 5-(pentadec-8-ynyl)resorcinol dimethyl ether which was selectively converted into the 8-(Z)-alkene.Dmethylation with lithium iodide gave 5-<(Z)-pentadec-8-enyl>resorcinol which was identical to 'cardol monoene'.Reaction of 7-(3,5-dimethoxyphenyl)heptyl bromide with lithium derivative of OH-protected propargyl alcohol, gave after acidic treatment 10-(3,5-dimethoxyphenyl)dec-2-yn-1-ol, the bromide of which with pent-1-ynylmagnesium bromide afforded 5-pentadec-8,11-diynylresorcinol dimethyl ether.Selective hydrogenation yielded 5-<(ZZ)-pentadeca-8,11-dienyl>resorcinol dimethyl ether identical with the dimethyl ether of 'cardol diene.'

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