Process for producing hydroxyalkane carboxylic acid amides

C - Chemistry – Metallurgy – 07 – C

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C07C 235/06 (2006.01) C07C 231/02 (2006.01) C07D 295/182 (2006.01) C07D 295/185 (2006.01)

Patent

CA 2127292

Abstract A process is described for the production of hydroxyalkane carboxylic acid amides of general formula I Image (I), in which n represents a whole number from 1 to 20 and R1 and R2 each mean alkyl groups with a maximum of 8 carbon atoms or together mean an alkylene group with 4 to 8 carbon atoms optionally interrupted by an oxygen atom or a nitrogen atom, from hydroxyalkane carboxylic acids of general formula II HO-CnH2n-COOH (II), in which n has the above-mentioned meaning and amines of general formula III Image (III), in which R1 and R2 have the above-mentioned meanings that is characterized in that the hydroxyalkane carboxylic acid is refluxed in a one-pot reaction with 10 to 30 mol of acetyl chloride per mol of acid each, the excess acetyl chloride is distilled off after acetylation has taken place, the residue is refluxed with 1.5 to 5 mol of thionyl chloride per mol of acid, the thionyl chloride is removed by distillation after acid chloride formation has taken place, the residue is dissolved in a dialkyl ether with 4 to 8 carbon atoms, the solution obtained is placed proportionately in an aqueous solution of the amine cooled to 0°C to 10°C and the acetate group is cleaved off after amide formation has taken place by treatment with aqueous sodium hydroxide solution at a reaction temperature of 10°C to 30°C.

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