4-Chloro-4-alkoxy-1,1,1-trifluoro-2-butanones, their preparation and their use in preparing 4-alkoxy-1,1,1-trifluoro-3-buten-2-ones
View Patent ↗4-Chloro-4-alkoxy-1,1,1-trifluoro-2-butanones, prepared by reacting alkyl vinyl ethers with trifluoroacetyl chloride, are useful for preparing 4-alkoxy-1,1,1-trifluoro-3-buten-2-ones.
1. A 4-chloro-4-alkoxy-1,1,1-trifluoro-2-butanone of the formula:
in which R represents a C 1 -C 8 alkyl or phenyl.
2. A process for the preparation of 4-chloro-4-alkoxy-1,1,1-trifluoro-2-butanones of the formula:
in which R represents a C 1 -C 8 alkyl or phenyl
which comprises contacting an alkyl vinyl ether of the formula
in which R is as previously defined with trifluoroacetyl chloride either neat or in the presence of an anhydrous organic solvent at a temperature from about −10° C. to about 35° C.
3. A process for the preparation of 4-alkoxy-1,1,1-trifluoro-3-buten-2-ones of the formula:
in which R represents a C 1 -C 8 alkyl or phenyl which comprises contacting a 4-chloro-4-alkoxy-1,1,1-trifluoro-2-butanone of the formula:
in which R represents a C 1 -C 8 alkyl or phenyl, with a sulfoxide or a formamide catalyst of the formula
in which R 2 independently represents C 1 -C 8 alkyl or phenyl, and
R 3 independently represents H, C 1 -C 8 alkyl or phenyl, in the presence of an anhydrous organic solvent at a temperature from about −10° C. to about 20° C.
4. A process for the preparation of 4-alkoxy-1,1,1-trifluoro-3-buten-2-ones of the formula:
in which R represents a C 1 -C 8 alkyl or phenyl which comprises:
a) contacting an alkyl vinyl ether of the formula
in which R is as previously defined with trifluoroacetyl chloride either neat or in the presence of an anhydrous organic solvent at a temperature from about −10° C. to about 35° C. to provide a 4-chloro-4-alkoxy-1,1,1-trifluoro-2-butanones of the formula:
in which R represents a C 1 -C 8 alkyl or phenyl; and
b) contacting the 4-chloro-4-alkoxy-1,1,1-trifluoro-2-butanone of the formula:
in which R represents a C 1 -C 8 alkyl or phenyl, with a sulfoxide or a formamide catalyst of the formula
in which R 2 independently represents C 1 -C 8 alkyl or phenyl, and
R 3 independently represents H, C 1 -C 8 alkyl or phenyl, in the presence of an anhydrous organic solvent at a temperature from about −10° C. to about 20° C.