L. D. Buyck, J. Vanslembrouck, N. Kimpe
Sep 1, 2010
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0
Influential Citations
4
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Journal
Bulletin des Sociétés Chimiques Belges
Abstract
Trans-1,2-cyclohexanediol was quantitatively converted into 3,3,6,6-tetrachloro-1,2-cyclohexanedione (2) by treatment with chlorine in dimethylformamide. The hydrate of the dione was oxidized by aqueous potassium permanganate to afford the title acid 1 in 91% overall yield. An alternative low cost preparation was elaborated, providing 2 in 61–74% yield starting from cyclohexanone in a three step procedure without isolation of intermediates. The reaction sequence involves substitution of α-dichloro- and trichlorocyclohexanones by sodium acetate in acetic acid and chlorination of the resulting 2-hydroxy- and 2-acetoxy-2-cyclohexenones in dimethylformamide.