Process for producing trifluoromethylacetophenones
AssigneeNIPA Hardwicke, Inc.
InventorJ. E. Hardwicke, III
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Abstract
The present invention provides high purity trifluoromethylacetophenones of the general formula: F.sub.3 C--(C.sub.6 H.sub.4)-(C.dbd.O)--CH.sub.3 wherein the position of the CF.sub.3 -- group on the aromatic ring may be in the 2-, 3-, or 4- position relative to the acetyl, --(C.dbd.O)--CH.sub.3, group, said trifluoromethylacetophenone being substantially free of other organic or inorganic materials, wherein said trifluoromethylacetophenones are produced by a novel high yield process.
Claims9
A process for the production of a trifluoromethylacetophenone at a purity of at least about 90% and yield of at least about 90% of the general formula:
- F.sub.3 C--(C.sub.6 H.sub.4)-(C.dbd.O)--CH.sub.3
- wherein the position of the CF.sub.3 -- group on the aromatic ring may be in the 2-, 3-, or 4- position relative to the acetyl, --(C.dbd.O)--CH.sub.3, group, said process comprising the steps of:
- (a) reacting a trifluoromethylbenzoyl halide of the general formula:
- F.sub.3 C--(C.sub.6 H.sub.4)-(C.dbd.O)--X
- wherein the position of the CF.sub.3 -- group on the aromatic ring may be in the 2-, 3-, or 4- position relative to the acetyl, --(C.dbd.O)--CH.sub.3, group and X is a halogen atom selected from the group consisting of fluorine, chlorine, bromine, and iodine, with a diorganoamine of the general formula
- R.sub.2 NH
- wherein each R is independently a straight or branched chain monovalent aliphatic hydrocarbon with from 1 to about 6 carbon atoms in the presence of an aqueous base, used as an acid acceptor, resulting in the formation of a N,N-dialkyltrifluoromethylbenzamide of the general formula:
- CF.sub.3 --(C.sub.6 H.sub.4)-(C.dbd.O)--NR.sub.2
- wherein the position of the CF.sub.3 -- group on the aromatic ring may be in the 2-, 3-, or 4- position relative to the acetyl, --(C.dbd.O)--CH.sub.3, group, and each R is as defined above;
- and
- (b) adding a methyl Grignard reagent to said benzamide followed by acidification with an aqueous acidification reagent to form said trifluoromethylacetophenone product.
Dependencies are inferred from the claim text.