A SYNTHESIS OF 3,3,3-TRICHLORO-1,2-EPOXYPROPANE FROM THE TETRAHALOPROPANE DERIVED FROM A CARBON TETRAHALIDE AND ETHYLENE

Abstract

A study has been made of the reactions involving the addition of bromotrichloromethane to ethylene to give 3-bromo-1,1,1-trichloropropane, subsequent dehydrohalogenation of this to 3,3,3-trichloro-1-propene, and the isomerization of the latter to 1,1,3-trichloro-1-propene; the experimental conditions have been improved so that the minimum yield obtained in any one step is 78%. The 1,1,3-trichloro-1-propene is converted to a chlorohydrin in 36% yield by reaction with tert-butyl hypochlorite, and the chlorohydrin is converted in 61% yield to 3,3,3-trichloro-1,2-epoxypropane by treatment with base. The reaction of 3,3,3-trichloro-1-propene with methoxide ion to form 1,1-dichloro-3-methoxy-1-propene provides another example of an SN2′ reaction.