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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Hydroxylation of anthraquinones in oleum and in sulfuric acid

HJ Banks, DW Cameron and WD Raverty

Australian Journal of Chemistry 31(10) 2271 - 2282
Published: 1978

Abstract

The anthraquinone emodin (9) was rapidly and efficiently converted into catenarin (13) by treatment with a mixture of oleum and boric acid at room temperature. Chrysophanol (15) similarly gave islandicin (16), while related anthraquinones were hydroxylated in essentially the same way, though none as rapidly as emodin. The specificity of such processes is synthetically useful in generally involving substitution of the less highly hydroxylated ring. This is in contrast to hydroxylation with persulfate in sulfuric acid which, for emodin, occurred chiefly in the more highly hydroxylated ring, as did sulfonation.

https://doi.org/10.1071/CH9782271

© CSIRO 1978

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