49775-33-9Relevant articles and documents
PRACTICAL SYNTHESIS OF 2,2,5,5-TETRACHLORO-1,6-HEXANEDIOIC ACID, FROM TRANS-1,2-CYCLOHEXANEDIOL OR CYCLOHEXANONE, INVOLVING OXIDATION OF 3,3,6,6-TETRACHLORO-1,2-CYCLOHEXANEDIONE
Buyck, Laurent de,Vanslembrouck, Jan,Kimpe, Norbert de,Verhe, Roland,Schamp, Niceas
, p. 913 - 918 (2007/10/02)
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 91percent overall yield.An alternative low cost preparation was elaborated, providing 2 in 61-74percent yield starting from cyclohexanone in a three step procedure without isolation of intermediates.The reaction seqence 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.