PREPARATION OF 4 - ACYLATED ARYL (BENZYL o - SUBSTITUTED) ETHERS BY FRIEDEL -CARAFTS TYPE REACTIONS

摘要

A process for preparing 4-acylated aryl o-substituted benzyl ethers of the formula R2mR3 OYR OR1O X where R is hydrogen, halogen, cyano; C1-C4-alkyl, C1-C4-alkoxy; X is CH2, CH-CH3, CH-CH2-CH3, CH- OCH3 or N-OCH3; Y is oxygen, sulfur, direct linkage or nitrogen which can carry a hydrogen atom, a C1-C4-alkyl group or a C1-C4-alkoxy group; m is 0, 1, 2 or 3, it being possible for the R2 radicals to be different when m is 2 or 3; R1 is hydrogen; C1-C5-alkyl, C3-C5-alkenyl, C3-C5-alkynyl or C1-C4-alkoxy, it being possible for these groups to carry one or two halogen atoms; R2 is cyano, halogen, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl; R3 is C1-C12-alkyl; C1-C12-haloalkyl; C3-C8-cycloalkyl; or an unsubstituted or substituted mono-to trinuclear aromatic system which may, besides carbon atoms, contain one to four nitrogen atoms or one to three hetero atoms selected from the group comprising two nitrogen atoms and one oxygen or sulfur atom, it also being possible for the aromatic radicals to carry one to three substituents selected from the group comprising halogen; C1-C4-alkyl; C1-C4-alkoxy; which comprises reacting an aryl benzyl ether of the formula R2m20 OR HR1Y XO where X, Y, R, R1, and m have the abovementioned meanings, with a carbonyl halide of the formula R3-CO-halogen or with a carboxylic anhydride of the formula R3-COO-CO-R3 or with a carboxylic sulfonic anhydride of the formula R3COO- SO2-R4 where R3 has the abovementioned meaning, and R4 is C1-C4-alkyl, C1-C4-haloalkyl or aryl, in the presence of an acid and in the presence or absence of a diluent.