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Synthesis 2012(5): 805-809  
DOI: 10.1055/s-0031-1289695
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Practical Synthesis of 1,4,5,8-Tetramethoxyanthracene from Inexpensive and Readily Available 1,8-Dihydroxyanthraquinone

Tushar S. Navale, Rajendra Rathore*
Marquette University, Department of Chemistry, P.O. Box 1881, Milwaukee, WI 53201, USA
Fax: +1(414)2887066; e-Mail: Rajendra.Rathore@marquette.edu ;
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Publikationsverlauf

Received 1 November 2011
Publikationsdatum:
06. Februar 2012 (online)

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Abstract

The preparation of gram quantities of 1,4,5,8-tetra­methoxyanthracene from commercially available and inexpensive 1,8-dihydroxyanthraquinone is described. The key steps in the synthesis involve bromination of 1,8-dimethoxyanthracene to form 1,8-dibromo-4,5-dimethoxyanthracene followed by Cu(I) catalyzed replacement of bromo substituents with methoxy groups. The contrasting reports concerning the preparation of 1,8-dimethoxy­anthracene from 1,8-dimethoxyanthraquinone using zinc dust in refluxing acetic acid are also discussed.

Key words

anthraquinones - polycyclic aromatic hydrocarbons - copper(I) bromide - bromination - zinc

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