Abstract: A multi-step process is described for preparing a methoxytrifluoromethylnaphthoic acid compound of formula ##STR1## from 1,5-dimethylnaphthalene and for preparing novel intermediate compounds of formula ##STR2## where X is chlorine or fluorine. Methoxytrifluoromethylnaphthoic acid is useful for preparing biologically active compounds such as naphthyl thioamide derivatives which inhibit aldose reductase activity.

Abstract: A multi-step process is described for preparing a methoxytrifluoromethylnaphthoic acid of formula ##STR1## from 1-methyl-5-naphthoic acid and for preparing novel intermediate compounds of formula ##STR2## where X is chlorine or fluorine. Methoxytrifluoromethylnaphthoic acid is useful for preparing biologically active compounds such as naphthyl thioamide derivatives which inhibit aldose reductase activity.

Abstract: A process for the preparation of fluoroanthranilic acid compounds comprises(A) reacting ammonium fluorophthalamate or a fluorophthalamic acid of the formula ##STR1## where n is 1 or 2, with an alkali or alkaline earth metal hypochlorite to form the corresponding fluoroanthranilic acid of the formula ##STR2## where n is as previously defined.

Abstract: A process for the preparation of meta-substituted diaryl ethers comprises reacting an ortho-haloaryl compound with a phenol compound in a non-aqueous medium in the presence of an alkaline metal base. In a specific embodiment m-phenoxytoluene is prepared by reacting orthochlorotoluene with phenol in the presence of an alkaline metal hydroxide in a substantially non-aqueous liquid medium.

Abstract: Fluorophthalamic acids characterized by the formula ##STR1## wherein n is 1 or 2, are prepared by the steps of(A) reacting a chlorophthalic anhydride of the formula ##STR2## where n is as defined previously, with potassium fluoride or cesium fluoride to form a fluorophthalic anhydride of the formula ##STR3## where n is as previously defined, and (B) reacting the fluorophthalic anhydride with ammonia to form an ammonium salt of a fluorophthalamic acid, and(C) acidifying the ammonium salt to form a fluorophthalamic acid.

Abstract: Ammonium salts of fluorophthalamic acids characterized by the formula ##STR1## wherein n is 1 or 2, are prepared by the steps of (A) reacting a chlorophthalic anhydride of the formula ##STR2## where n is as defined previously, with potassium fluoride or cesium fluoride to form a fluorophthalic anhydride of the formula ##STR3## where n is as previously defined, and (B) reacting the fluorophthalic anhydride with ammonium to form an ammonium salt of a fluorophthalamic acid.

Abstract: A process for the preparation of fluoroaniline compounds comprises the steps of(A) reacting an ammonium fluorophthalamate or a fluorophthalamic acid of the formula ##STR1## where n is 1 or 2 with an alkali or an alkali earth metal hypochlorite to form the corresponding fluoroanthranilic acid; and(B) decarboxylating the fluoroanthranilic acid by reaction with a mineral acid to form the corresponding fluoroaniline of the formula ##STR2## where n is as previously defined.

Abstract: The present invention provides a novel organic compound, (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid, and a process for the preparation thereof comprising the steps of:a. converting (3-trifluoromethyl)-benzotrichloride to the corresponding benzoyl chloride,b. cyanation of the benzoyl chloride to produce the corresponding benzoyl cyanide,c. hydrolyzing the benzoyl cyanide to produce the corresponding keto-acid, andd. hydrogenating the keto-acid to produce (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid.

Abstract: The present invention relates to a novel organic compound, phenyl beta-chloro-alpha-hydroxy-beta-(3-trifluoromethylphenyl)ethyl ketone. This compound may be produced by:(a) condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone,(b) epoxidation of the substituted chalcone to produce the corresponding epoxide, and(c) converting the epoxide to a chlorohydrin, phenyl beta-chloro-alpha-hydroxy-beta-(3-trifluoromethylphenyl)ethyl ketone.

Abstract: The present invention provides a novel process for the production of methyl or ethyl ester of (3-trifluoromethylphenyl)-acetic acid. The process comprises the steps of:(a) converting (3-trifluoromethyl)-benzotrichloride to the corresponding benzoyl chloride,(b) cyanation of the benzoyl chloride to produce the corresponding benzoyl cyanide,(c) hydrolyzing the benzoyl cyanide to produce the corresponding keto-acid,(d) hydrogenating the keto-acid to produce (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid,(e) hydrogenating (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid in the presence of glacial acetic acid to produce the corresponding substituted acetic acid, and(f) esterifying the substituted acetic acid using an alcohol selected from the group consisting of methyl and ethyl to obtain the corresponding methyl or ethyl ester of (3-trifluoromethylphenyl)-acetic acid.

Abstract: The present invention relates to a novel organic compound, (3-trifluoromethyl)-benzoyl cyanide, and a process for the preparation thereof comprising(a) converting (3-trifluoromethyl)-benzotrichloride to the corresponding benzoyl chloride,b) cyanation of the benzoyl chloride to produce the corresponding benzoyl cyanide, (3-trifluoromethyl)-benzoyl cyanide.

Abstract: The present invention provides a novel process for the production of 1-phenyl-3-(3-trifluoromethylphenyl)-2-propanone. The process comprises the steps of:(a) condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone,(b) epoxidation of the substituted chalcone to produce the corresponding epoxide,(c) converting the epoxide to a chlorohydrin,(d) catalytic hydrogenolysis of the chlorohydrin to produce a diol and subsequently converting the diol into the corresponding alcohol, and(e) oxidizing the alcohol to produce 1-phenyl-3-(3-trifluoromethylphenyl)-2-propanone.

Abstract: The present invention relates to a novel organic compound, phenyl alpha,beta-epoxy-beta-(3-trifluoromethylphenyl)ethyl ketone. This compound may be produced by:(a) condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone, and(b) epoxidation of the substituted chalcone to produce the corresponding epoxide, phenyl alpha,beta-epoxy-beta-(3-trifluoromethylphenyl)ethyl ketone.

Abstract: The present invention relates to a novel organic compound, 1-phenyl-3-(3-trifluoromethylphenyl)-2-propanol. This compound may be produced by:a. condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone,b. epoxidation of the substituted chalcone to produce the corresponding epoxide,c. converting the epoxide to a chlorohydrin, andd. catalytic hydrogenolysis of the chlorohydrin to produce a diol and subsequently converting the diol into the corresponding alcohol, 1-phenyl-3-(3-trifluoromethylphenyl)-2-propanol.

Abstract: The present invention relates to a novel organic compound, 1-phenyl-3-(3-trifluoromethylphenyl)-1,2-propane diol. This compound may be produced by:(a). condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone,(b). epoxidation of the substituted chalcone to produce the corresponding epoxide,(c). converting the epoxide to a chlorohydrin, and(d). catalytic hydrogenolysis of the chlorohydrin to produce a diol, 1-phenyl-3-(3-trifluoromethylphenyl)-1,2-propan-diol.