Novel Regioselectivity under Conformational Control in the Methylation of 2,3-Dihydroxy-1-naphthaldehyde

DOI: 10.1039/c39850000502

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 502 - 503 (1985)

Update date:2022-08-24

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Authors:

Dean, Francis M.

El-Kass, Gassan

Prakash, Lalit

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Article abstract of DOI:10.1039/c39850000502

Methylation of 2,3-dihydroxy-1-naphthaldehyde with iodomethane and potassium carbonate in acetone selectively etherifies the chelated 2-hydroxy group because ionisation of this destroys the stabilising hydrogen bond and allows the formyl group to take up a preferred conformation away from the reaction centre.

Full text of DOI:10.1039/c39850000502

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