The acetylation of naphthoquinones. The synthesis of 3-acetyl-5-methoxy- and 3-acetyl-5,7-dimethoxy-1,4-naphthoquinones

Chorn, T.A., Giles, R.G.F., Green, I.R., Hugo, V.I., Mitchell, P.R.K. and Yorke, S.C. (1984) The acetylation of naphthoquinones. The synthesis of 3-acetyl-5-methoxy- and 3-acetyl-5,7-dimethoxy-1,4-naphthoquinones. Journal of the Chemical Society, Perkin Transactions 1 . pp. 1339-1343.

Abstract

The conversion of 5-methoxy- and 5,7-dimethoxy-1,4-naphthoquinones into their 3-acetyl derivatives is described. A key step is the Fries rearrangement of 1,5-dimethoxy-4-acetoxynaphthalenes to the corresponding 3-acetyl-4-naphthols with boron trifluoride–diethyl ether. Alternative Fries rearrangement of 1-acetoxy-4-hydroxy-5-methoxynaphthalenes gave the 3-acetylquinols, involving meta migration of the acetyl group. A convenient new synthesis of 2-acetyl-1,4-naphthoquinone is also reported.

Item Type:	Journal Article
Publisher:	Royal Society of Chemistry
Copyright:	© 1984 Royal Society of Chemistry
URI:	http://researchrepository.murdoch.edu.au/id/eprint/35671

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