Hoechst Aktiengesellschaft

Clariant Corporation

Andreas Dierdorf

Theodor Papenfuhs

Siegfried Planker

Robert Cosmo

Helmut Bahrmann

Boy Cornils

Steffen Haber

Stefan Krause

Doris Neumann-Grimm

Nitro compound-reducing process

The present invention relates to a process for the preparation of 3-acetoxy-2-methylbenzoyl chloride by reacting an alkali metal salt of 3-aminonaph-thalene-1,5-disulfonic acid with alkali metal hydroxide and water in the weight ratio 1:(1 to 1.6):(1 to 1.6) at 220 to 320.degree. C. to give the dialkali metal salt of the 3-hydroxy-2-methylbenzoic acid, separating off insoluble constituents from the reaction mixture, then adjusting the reaction mixture to a pH of 11.5 to 13.5 by addition of acid and reacting with acetic anhydride at -5 to +25.degree. C., precipitating the 3-acetoxy-2-methylbenzoic acid by addition of acid, separating off the 3-acetoxy-2-methylbenzoic acid and reacting it with an inorganic acid chloride to give 3-acetoxy-2-methylbenzoyl chloride.

Process for the preparation of 3-acetoxy-2-methylbenzoyl chloride

The invention relates to a process for the preparation of 3-hydroxy-2-methylbenzoic acid and 3-acetoxy-2-methylbenzoic acid, which comprises reacting 3-chloro-2-methylphenol (3) with benzyl chloride to give 2-benzyloxy-6-chlorotoluene (4) subjecting this to a Grignard reaction with magnesium to give (3-benzyloxy-2-methylphenyl)magnesium chloride (5) reacting this with CO.sub.2 to give 3-benzyloxy-2-methylbenzoic acid (6) hydrogenating this or its alkali metal salts in the presence of a hydrogenation catalyst to give 3-hydroxy-2-methylbenzoic acid (2) and optionally acetylating this to give 3-acetoxy-2-methylbenzoic acid.

Process for the preparation of 3-hydroxy-2-methylbenzoic acid and

Process for the preparation of N-carboxymethyleneanthranilic acid esters of the formula (3) ##STR1## by reacting a compound of the formula (1) ##STR2## in which R' is hydrogen or a straight-chain or branched alkyl radical having 1 to 4 carbon atoms and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and independently of one another are hydrogen, halogen, NO.sub.2, a straight-chain or branched alkyl, alkoxy or halogenated alkyl radical having in each case 1 to 6 carbon atoms, with a glyoxylic acid ester of the formula (2)

Process for the preparation of N-carboxymethyleneanthranilic acid

The present invention relates to a process for the preparation of hydroxycarboxylic acid amides of the general formula (1): ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are hydrogen, halogen, cyano, a linear or branched alkyl, alkenyl, alkynyl or alkoxy group having 1 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a cycloalkyl group having 6 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms, R.sup.3 is hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms, R.sup.4 is hydrogen or a linear or branched alkyl group having 1 to 6 carbon atoms, or R.sup.3 and R.sup.4, together with the carbon atom to which they are attached, form a five- or six-membered cycloalkane ring, and n is an integer from 1 to 12, wherein an aniline of the general formula (2) ##STR2## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined in the formula (1), is reacted with a hydroxycarboxylic acid of the general formula (3) ##STR3## in which n is as defined in the formula (1), in the presence or absence of an inert solvent, at 150.degree. to 250.degree. C., and the constituents which are volatile under the reaction conditions are distilled out of the reaction mixture.

Hydroxycarboxylic acid anilides

The present invention relates to a process for the preparation of O-acylglycolanilides of the formula (1) ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are hydrogen, halogen, a nitro group, a cyano group, a straight-chain or branched alkyl, alkenyl, alkynyl or alkoxy group having from 1 to 12 carbon atoms, an aralkyl group having from 7 to 12 carbon atoms, a cycloalkyl group having from 6 to 12 carbon atoms or an aryl group having from 6 to 12 carbon atoms,. R.sup.3 is hydrogen or a straight-chain or branched alkyl group having from 1 to 12 carbon atoms, and R.sup.4 is an alkyl group having from 1 to 6 carbon atoms or is a substituted or unsubstituted phenyl radical, in which an aniline of the formula (2) ##STR2## in which R.sup.1, R.sup.2 and R.sup.3 have the same meaning as in formula (1), and an O-acylglycolic acid of the general formula (3) ##STR3## in which R.sup.4 has the same meaning as in formula (1), are reacted with an inorganic acid halide, optionally in the presence of an inert organic solvent, at from 20.degree. to 180.degree. C.

Process for the preparation of O-acylglycolanilides

The present invention relates to a process for the preparation of O-acyloxycarboxanilides of the formula (I) ##STR1## in which R is a radical having 1 to 6 carbon atoms, n is an integer from 1 to 10, R.sup.1 is hydrogen or an alkyl radical having 1 to 12 carbon atoms, R.sup.2 and R.sup.3 are identical or different and are hydrogen, an alkyl radical having 1 to 12 carbon atoms, an aryl radical having 6 to 12 carbon atoms, a cycloalkyl radical having 5 to 12 carbon atoms in the ring, an alkenyl or alkynyl radical having 3 to 12 carbon atoms, NO.sub.2, F, Cl, Br or CN, by reacting a chlorocarboxanilide of the formula (II) ##STR2## in which n, R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meaning, with an alkali metal carboxylate of the formula (III)

Process for the preparation of o-acyloxycarboxanilides

The present invention relates to a process for the preparation of hydroxycarboxanilides of the formula (1) ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are hydrogen, halogen, a nitro group, a cyano group, a straight-chain or branched alkyl, alkenyl, alkynyl or alkoxy group having 1 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a cycloalkyl group having 6 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms, R.sup.3 is hydrogen or a straight-chain or branched alkyl group having 1 to 12 carbon atoms and n is an integer from 1 to 12, by reacting a halocarboxanilide of the formula (2) ##STR2## in which R.sup.1, R.sup.2, R.sup.3 and n have the same meaning as in formula (1) and Hal is chlorine, bromine or iodine, with a basic compound in a solvent mixture comprising water and one or more polar aprotic solvents at a temperature of 40.degree. to 180.degree. C.

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Frankfurt-am-Main, Germany

Andreas Dierdorf