Carbon Tetrachloride → Ethanone, 2,2,2-trichloro-1-[4-(1,1-dimethylethyl)phenyl]-

Illustrative examples of compounds according to the general formula hereinbefore defined are: 2-chloro-4'-tert.butylacetophenone; 2,2-di-chloro-4'-tert.butylacetophenone; 2-chloro-4'-octylacetophenone; 2,2-di-chloro-4'-octylacetophenone; 2-chloro-4'-n-C8-13 -alkylacetophenone; 2,2-dichloro-4'-n-C8- alkylacetophenone; 2,2,2-trichloro-4'-n-C8-13 alkylacetophenone in which the alkyl groups range from 8-13 carbon atoms (derived from C8-13 alkylbenzene with the trade name Dobane 83 X); 2,2-dichloro-4'-octyloxyacetophenone; 2,2,2-trichloro-4'-octyloxyacetophenone; 2,2-dichloro2',4'-diisopropylacetophenone; 2,2,2-trichloro-2',4'-diisopropylacetophenone or mixtures of these compounds. Preferably, however, the new compund 2,2,2-trichloro-4'-tert.butylacetophenone is used. This compound may be prepared in an analogous way to that described in J.A.C.S. 72 (1950) pages 3952-3 for the preparation of trichloroacetophenone, namely by treating 4-tert.butylacetophenone with chlorine. The starting 4-tert.butylacetophenone may be obtained in the manner described in J.A.C.S. 68 (1946) page 1107 by a Friedel-Crafts acetylation of tert.butylbenzene with acetyl chloride in a solvent, such as carbon tetrachloride. The compound 2,2,2-trichloro-4'-tert.butylacetophenone may also be obtained in an analogous way to that described in Houben-Weyl 5/3 page 790 for the preparation of trichloro-2',4',6'-trimethylacetophenone. The compound may also be prepared directly by a Friedel-Crafts reaction of tert.butylbenzene with trichloroacetyl chloride in carbon disulphide as described in J. Indian Chem. Soc. 26 (1947) pages 287-9. It is also possible to use trichloro-acetonitrile instead of trichloro-acetyl chloride as described in J. Prakt. Chem. (2) 123 (1929) 313.

ORD record

ord-fc856c0bb9ed4608a4acf02a4ff4cdc5

Source dataset

uspto-grants-1978_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04115224