KR900701742A - Method for preparing O-substituted oxime compound - Google Patents

Abstract

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Description

Method for preparing O-substituted oxime compound

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Claims (10)

A method for producing a 0-substituted oxime compound of general formula (I) consisting of the following steps (a)-(d). (a) reacting an oxime compound of the following general formula (II) with an aqueous solution of an alkali metal hydroxide or alkaline earth metal hydroxide in an organic solvent, (b) azeotropic distillation of the reaction mixture of step (a) to remove some or all of the water from the reaction mixture to obtain a residual mixture consisting of the metal salt of the reaction solvent and an oxime compound, and (c) in the residual mixture. The oxime compound metal salt is reacted with an alpha halocarboxylic acid of the following general formula (III) in an excess molar ratio of more than two times, (d) Separate recovery of the 0-substituted auxin compound from the mixture of reaction solvent and excess oxime reactant. In the above general formulas, X is halogen, R ₁ and R ₂ are each hydrogen or substituted or unsubstituted, aryl, alkyl, cycloalkyl, alkenyl, alkylsulfinyl, arylsulfonyl, arylthio, alkoxy Substituted or unsubstituted, a group selected from the group consisting of alkyl, alkylthio, alkylsulfoyl and alalkyl, or R ₁ and R ₂ together form a cycloalkyl or cycloalkenyl group having 3-7 carbon atoms in the ring, Alkenyl or alkenylene chains, where possible substituents include one or more alkylthio, alkyl sulfinyl, alkaminocarbonyl, dialkylaminocarbonyl, alkylthiocarbonyl, alkyl, alkylsulfonyl, phenoxy, amido, alkoxy Carbonyl, alkoxy, nitro, arylthio, arylsulfinyl, perfluoroalkyl, cyano or fluorine and R ₃ is an organic radical. The process according to claim 1, wherein the reaction mixture to be subjected to azeotropic distillation in step (b) comprises water and at least one nonpolar non-reactive organic solvent which forms an azeotropic mixture when distilled with the oxime compound. . The process according to claim 2, wherein the reaction of step (a) is carried out in the presence of at least one nonpolar non-reactive organic solvent which forms an azeotrope when distilled together with water and an oxime compound. The process according to claim 1, wherein R ₃ is phenyl, alkenyl, alkyl or alkyl substituted with one or more amido, cyano or alkoxycarbonyl groups. The process according to claim 4, wherein R ₃ is alkyl or phenyl. The process according to claim 1, wherein the reaction solvent of step (d) and the excess oxime compound are recycled to step (a). The process according to claim 1, wherein R ₁ and R ₂ are each hydrogen, alkyl, phenyl or phenylalkyl. 2. The method of claim 1, wherein step (d) adds an amount of water to dissolve all or part of the solids present in the reaction mixture to the reaction mixture and neutralizes the pH of the mixture to 7 to free excess oxime salt. Converting to an oxime compound and removing it from the reaction mixture, and then precipitating and collecting all or part of the 0-substituted oxime compound by lowering the pH of the mixture to 1 or less. The method according to claim 8, wherein the free oxime compound is removed by azeotropic distillation or extraction with a reaction condition. The method according to claim 8, wherein the 0-substituted oxime compound is collected by filtration or extraction with an organic solvent. ※ Note: The disclosure is based on the initial application.