L. D. Buyck, Guido Detienne, M. Boelens
Sep 1, 2010
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Journal
Bulletin des Sociétés Chimiques Belges
Abstract
Normally 3-pentanone reacts with boiling sulfuryl chloride to yield a mixture of dichlorinated compounds. The production of 2,2,4-trichloro-3-pentanone (97% selectivity; 88–93% yield) can be promoted by the catalytic combination of a soluble strong acid and its salt with an organic base. Using chlorosulfonic acid or p-toluenesulfonic acid (82 mmol/mol ketone) combined with N,N-dimethyloctylamine or N-formylmorpholine (50 mmol) the trichlorination step was reached after less than 6h at 97°C. Each additive alone gave a poor result. The trichlorination can be accomplished in 1h at 60–70°C with chlorine and some excess of dimethylformamide, but the catalytic procedure is advantageous for its practical convenience and for avoiding DMF.HCI as a waste.