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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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Publication History

Received 1 November 2011
Publication Date:
06 February 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

    References

  • 1a Navale TS. Thakur K. Rathore R. Org. Lett.  2011,  13:  1634 
    Search in Google Scholar
  • 1b Modjewski MJ. Shukla R. Lindeman SV. Rathore R. Tetrahedron Lett.  2009,  50:  6687 
    Search in Google Scholar
  • 1c Wadumethrige SH. Rathore R. Org. Lett.  2008,  10:  5139 
    Search in Google Scholar
  • 1d Banerjee M. Shukla R. Rathore R. J. Am. Chem. Soc.  2009,  131:  1780 
    Search in Google Scholar
  • 1e Banerjee M. Lindeman SV. Rathore R. J. Am. Chem. Soc.  2007,  129:  8070 
    Search in Google Scholar
  • 1f Banerjee M. Vyas VS. Lindeman SV. Rathore R. Chem. Commun.  2008,  1889 
  • 1g Navale TS. Zhai L. Lindeman SV. Rathore R. Chem. Commun.  2009,  2857 
  • 1h Rathore R. Abdelwahed SH. Guzei IA. J. Am. Chem. Soc.  2003,  125:  8712 
    Search in Google Scholar
  • 1i Chebny VJ. Gwengo C. Gardinier JR. Rathore R. Tetrahedron Lett.  2008,  49:  4869 
    Search in Google Scholar
  • 2a Chiriboga X. Gilardoni G. Magnaghi I. Finzi PV. Zanoni G. Vidari G. J. Nat. Prod.  2003,  66:  905 
    Search in Google Scholar
  • 2b Boniface PJ. Cambie RC. Carroll DR. Marsh NF. Milbank JBJ. Rutledge PS. Woodgate PD. Aust. J. Chem.  1994,  47:  441 
    Search in Google Scholar
  • 2c Springer JW. Moore TA. Moore AL. Gust D. Groy TL. Acta Crystallogr., Sect. E: Struct. Rep. Online  2002,  58:  o1145 
    Search in Google Scholar
  • 2d Cory RM. McPhail CL. Dikmans AJ. Tetrahedron Lett.  1993,  34:  7533 
    Search in Google Scholar
  • 2e Quast H. Fuchsbauer HL. Chem. Ber.  1986,  119:  2414 
    Search in Google Scholar
  • 3a Lou K. Prior AM. Wiredu B. Desper J. Hua DH. J. Am. Chem. Soc.  2010,  132:  17635 
    Search in Google Scholar
  • 3b Jing C. Zhu X.-Z. Chen C.-F. J. Org. Chem.  2010,  75:  7420 
    Search in Google Scholar
  • 4a Zhu X.-Z. Chen C.-F. J. Org. Chem.  2005,  70:  917 
    Search in Google Scholar
  • 4b Pei B.-J. Chan W.-H. Lee AW.-M. Org. Lett.  2011,  13:  1774 
    Search in Google Scholar
  • 5a Norvez S. J. Org. Chem.  1993,  58:  2414 
    Search in Google Scholar
  • 5b Gaeta C. Vysotsky MO. Bogdan A. Boehmer V. J. Am. Chem. Soc.  2005,  127:  13136 
    Search in Google Scholar
  • 6a Norvez S. Tournilhac F.-G. Bassoul P. Herson P. Chem. Mater.  2001,  13:  2552 
    Search in Google Scholar
  • 6b Norvez S. Simon J. Chem. Commun.  1990,  1398 
  • 7 Quast H. Fuchsbauer HL. Chem. Ber.  1986,  119:  1016 
    Search in Google Scholar
  • 8 Almlof JE. Feyereisen MW. Jozefiak TH. Miller LL. J. Am. Chem. Soc.  1990,  112:  1206 
    Search in Google Scholar
  • 9 Fitzgerald JJ. Drysdale NE. Olofson RA. Synth. Commun.  1992,  22:  1807 
    Search in Google Scholar
  • 10 Fitzgerald JJ. Drysdale NE. Olofson RA. J. Org. Chem.  1992,  57:  7122 
    Search in Google Scholar
  • 11 Lu L. Chen Q. Zhu X. Chen C. Synthesis  2003,  2464 
  • 12 Shyamasundar N. Caluwe P. J. Org. Chem.  1981,  46:  809 
    Search in Google Scholar
  • 13a Cameron DW. Schutz PE. J. Chem. Soc.  1967,  2121 
  • 13b Hui CW. Mak TCW. Wong HNC. Tetrahedron  2004,  60:  3523 
    Search in Google Scholar
  • 14 Capdevielle P. Maumy M. Tetrahedron Lett.  1993,  34:  1007 
    Search in Google Scholar
  • 15a Nishio M. Hirota M. Umezawa Y. The CH/π Interaction. Evidence, Nature, and Consequences   Wiley-VCH; New York: 1998. 
  • 15b Shukla R. Lindeman SV. Rathore R. Chem. Commun.  2007,  3717 ; and references cited therein