1,4-Naphthoquinone → 1,4-Naphthoquinone

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Reaction Steps

It is known from German Pat. No. 739,438, to obtain anthraquinone by reaction of 1,4-naphthoquinone with excess 1-acetoxybutadiene at the reflux temperature. However, the yield is only 57% of theory. Furthermore it is known, from Liebig's Ann. Chem. volume 568 (1950), page 28, to warm 1,4-naphthoquinone with excess 1-acetoxybutadiene in acetic acid, separate off the resulting anthraquinone (19% of theory), isolate from the reaction solution the addition product first formed from 1,4-naphthoquinone and 1-acetoxybutadiene, namely 1-acetoxy-1,4,4a,9a-tetrahydroanthraquinone, and convert this into anthraquinone by means of methanolic potassium hydroxide solution in the presence of air. While this process gives a total yield of anthraquinone of about 80% of theory, it is unsuitable for large scale industrial use.

Provenance & Evidence