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        Synthesis  2012(5): 805-809  
DOI: 10.1055/s-0031-1289695
   DOI: 10.1055/s-0031-1289695
PAPER
© Georg Thieme Verlag
      Stuttgart ˙ New YorkA Practical Synthesis of 1,4,5,8-Tetramethoxyanthracene from Inexpensive and Readily Available 1,8-Dihydroxyanthraquinone
Further Information
            
               
                  
                        
                              Received
                              1 November 2011 
                      
Publication Date:
06 February 2012 (online)
            
         
      
   Publication History
Publication Date:
06 February 2012 (online)

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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