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Synthesis 1992; 1992(12): 1287-1291
DOI: 10.1055/s-1992-26360
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Synthesis of Tetra- and Pentasubstituted Benzenes from Dimedone and Derivatives

Peter H. Nelson* , Janis T. Nelson
  • *Institute of Organic Chemistry, Syntex Research, 3401 Hillview Ave., Palo Alto, California 94304, USA
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Publication Date:
29 April 2002 (online)

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Treatment of dimedone (5,5-dimethylcyclohexane-1,3-dione) and derivatives with one molar equivalent of sulfuric acid in trifluoroacetic anhydride leads, via sulfonation and a 1,2-methyl group migration, to a variety of dimethylresorcinol derivatives. The reaction has been performed on substrates bearing ester, alkoxy, halo and amino substituents to produce a variety of polysubstituted benzenes. Transient sulfonated intermediates were observed by NMR.