1. Field of the Invention
This invention relates to a new method for the production of certain 2,2-diorgano-1-indanones. Various indanones of this class such as 2,2-dimethyl-1-indanone and 2,2-diethyl-1-indanone are valuable intermediates in the production of pharmaceuticals. For example, 2,2-dimethyl-1-indanone is used in the synthesis of the antiallergic agent 4-(6'-chloro-2',2'-dimethylinden-1'-ylidene)-1-methylpiperidine, the anti-inflammatory and antiarthritic 2,2-dimethylindane-5-acetic acid, and other bioactive compounds such as coumarins.
2. Description of Related Art
The following information is disclosed in accordance with the terms of 37 CFR 1.56, 1.97 and 1.98.
U.S. Pat. No. 4,166,131, issued Aug. 28, 1979 to Payne, discloses the preparation of 2,2-dialkyl-1-indanones by the cyclization of the corresponding 2,2-dialkyl-3-phenyl (or substituted phenyl) propionic acid in the presence of a mineral acid, or alternatively, the cyclization of an acid chloride of such acid with a Friedel-Crafts catalyst, e.g. aluminum chloride. Specifically disclosed is the preparation of 2,2-dimethyl-1-indanone by the cyclization of .alpha.,.alpha.-dimethyldihydrocinnamic acid using polyphosphoric acid as catalyst.
U.S. Pat. No. 3,385,895 issued May 28, 1968 to Bruson et al. discloses the preparation of .beta.-disubstituted-.alpha.-indanones such as 2,2-dimethylindanone by reacting any of certain halogenated aliphatic ethers with carbon monoxide and an aromatic compound, e.g., benzene, in the presence of aluminum chloride or aluminum bromide. A similar process is disclosed by these patentees in Bruson et al., J. Org. Chem., 32, 3356-3362 (1967), wherein a halogenated hydrocarbon such as neophyl chloride or 2-chloro-2-methyl-3-phenylpropane is reacted with benzene and carbon monoxide in the presence of aluminum chloride to yield a .beta.-disubstituted-.alpha.-indanone such as 2,2-dimethyl-1-indanone.
Japanese Patent No. 74/10949 granted Mar. 13, 1974 to Kobayashi et al. (C. A. 82:125165g), describes the reaction of a 1,2-epoxide such as isobutylene oxide, carbon monoxide, and benzene in the presence of a Friedel-Crafts catalyst such as aluminum chloride to yield an indanone such as 2,2-dimethyl-1-indanone.
Warrick et al., J. Am. Chem. Soc., 84, 4095-4100 (1962) discloses the cyclization of 2,2-dimethyl-3-phenylpropionic acid with anhydrous HF to produce 2,2-dimethyl-1-indanone.
Japanese Kokai Patent No. SHO 55 [1980]-27147, published Feb. 27, 1980, discloses the formation of aryl-substituted carboxylic acids, e.g., ibuprofen, by reacting an aryl-substituted alcohol, e.g., 1-(4'-isobutylphenyl)ethanol (IBPE), with carbon monoxide and water in the presence of a hydrogen fluoride catalyst. Also disclosed generally is the synthesis of aryl-substituted alcohols by reducing the corresponding ketones.
Czech Patent No. CS 219,752 of Sept. 15, 1985, (C. A. 104:109233v), discloses a process of making ibuprofen from isobutylbenzene including the step of reducing 4-isobutylacetophenone (IBAP) to IBPE using lithium aluminum hydride as reductant.
D. Nightingale et al., J. Org. Chem., 14, 1089-1093 (1949), teach at page 1090 the hydrogenation of various aromatic ketones, including n-butyrophenone, 4-methyl-n-butyrophenone, and 2,4-dimethyl-n-butyrophenone, to produce the corresponding carbinol.