PROCESS FOR THE PREPARATION OF MIXTURES OF ISOMERS OF O-PHENOXYALKYLHYDROXYLAMINES OR O-PHENOXYALKYLOXIMES

摘要

A process is disclosed for producing isomer mixtures from Ophenoxyalkylhydroxyl amines Ia: H2N-O-CH2-CH(R1)-O-Ar and Ib: H2N-O-CH(R1)-CH2-O-Ar (wherein R1 represents alkyl, Ar where appropriate a substituted phenyl) and the corresponding salt mixtures. This process involves the following steps: (a) an isomer mixture of O-(2-hydroxyethyl)-oximes (IIa) and (IIb) (in which R2 is an alkyl and R3 is an alkyl or alkoxy, or R2 and R3 together with the common C atom form a 5-7 member ring) is converted by reaction with a sulphonyl halogenide of formula (III): Hal-SO2-R4 (wherein R4 represents an organic group and Hal is a halogen) in the presence of a base to form the corresponding sulphonate mixture of (IVa) and (IVb); (b) this sulphonate mixture is reacted in the presence of a base with a phenol of formula (V): HOAr to produce a mixture of O-phenoxyalkyloximes of general formulae (VIa) and (VIb); (c) the mixture is hydrolysed in the presence of an acid and, if required, (d) the O-phenoxyalkylhydroxyl amines (Ia) and (Ib) are released from the resulting salts using a mineral base. The O-phenoxyalkylhydroxyl amines (Ia/Ib) and their precursors (VIa/VIb) are important intermediate products for plant protective agents and drugs.