- Formation of dimer-type ketals in the reaction of 2,4,6-trichlorophenol and 2,4,6-trichloro-m-cresol with calcium hypochlorite in methanol: Conversion to quinones and other compounds
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2,4,6-Trichlorophenol (2) and 2,4,6-trichloro-m-cresol (5) react with calcium hypochlorite (Ca(OCl)2) in MeOH to give respectively dimer-type ketals 2-(2′,4′,6′-trichlorophenoxy)-4,4-dimethoxy-6 -chlorocyclohexadien-2,5-one (6) and 2-(3′-methyl-2′,4′,6′-trichlorophenoxy)-4, 4-di-methoxy-5-methyl-6-chlorocyclohexadien-2,5-one (7). Ketal 6, which was too unstable to be isolated, and 7 hydrolyzed in H2O/HCl to 2-(2′,4′,6′-trichlorophenoxy)-6-chloro-1,4-ben-zoquinone (8) and 2-(3′-methyl-2′,4′,6′-trichlorophenoxy)-5 -methyl-6-chloro-1,4-benzoquinone (9), respectively. Ketal 6 and quinone 8 were also produced when 2 and Ca(OCl)2 reacted in DMF, followed by addition of MeOH and H2O, respectively. The mechanisms of these reactions are examined. Conversion of the ketals and quinones to other products is described.
- Heasley, Victor L.,Anderson, James D.,Bowman, Zachery S.,Hanley Jr., John C.,Sigmund, Geoffery A.,Van Horn, David,Shellhamer, Dale F.
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p. 6827 - 6830
(2007/10/03)
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- Barium manganate oxidation in organic synthesis: Part - V: Oxidation of phenols
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Oxidation of phenols, specially the hindered phenols has been carried out with barium manganate in non-aqueous media under heterogeneous conditions and the results of these studies are described in this paper.
- Srivastava,Venkataramani
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