Abstract
Trichloromethanesulphonyl chloride reacts with styrene to give 1-phenyl-1,3,3,3-tetrachloropropane and 1,3-diphenyl-1,5,5,5-tetrachloropentane, together with sulphur dioxide. Hydrolysis of 1-phenyl-1,3,3,3-tetrachloropropane to cinnamic acid (90% yield) is catalysed by ferric chloride, and occurs under conditions that do not markedly affect 1,1,1,3-tetrachlorooctane. Acetolysis of 1-phenyl-1,3,3,3-tetrachloropropane gives largely 1-phenyl-3,3,3-trichloropropyl acetate; reduction of this compound with lithium aluminium hydride gives 1-phenylpropanol, confirming the position of the acetate group. A mechanism is proposed to account for the formation of 1,1-dimethoxy-1-phenylprop-2-yne in the reaction of 1-phenyl-1,3,3,3-tetrachloropropane with excess methanolic potassium hydroxide. Reduction of 1,3-diphenyl-1,5,5,5-tetrachloropentane with lithium aluminium hydride provides a synthesis of 1,3-diphenylpentane
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