Preparation of 1-phenyl-2,2,2-trihalogeno-ethanol esters

US4127728A · kind A · utility

Assignee

• BAYER HEALTHCARE LLC · DE

Inventors

• Thomas Schmidt · Neustadt, DE
• Wolfgang Kramer · Wuppertal, DE
• Eckart Kranz

Key dates

• Filing date: Aug 24, 1976
• Grant date: Nov 28, 1978
• Expiry date: Aug 24, 1996

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C381/14
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for the preparation of a substituted 1-phenyl-2,2,2-trihalo-ethanol ester of the formula ##STR1## in which R is alkyl, halogenoalkyl, alkoxy, cycloalkyl or optionally substituted phenyl, benzyl, phenoxy, or phenylsulfonyl, PA1 X is halogenoalkyl with 1-3 carbon atoms and 1-3 halogen atoms, PA1 Y is halogen, cyano, nitro, alkyl, alkoxy, alkylmercapto, sulfoalkoxy or optionally substituted methylenedioxy, and PA1 n is an integer from 0 to 3, Comprising reacting a compound of the formula ##STR2## WITH A HALOGENATED ALDEHYDE OF THE FORMULA EQU X CHO in the presence of a Friedel-Crafts catalyst at a temperature of about -70 to +100.degree. C thereby to form a complex alcoholate, and reacting the complex alcoholate with an acid halide of the formula ##STR3## OR WITH A CORRESPONDING ACID ANHYDRIDE AT A TEMPERATURE OF ABOUT -70 TO +100.degree. C. The reaction with the acid halide or anhydride is preferably carried out in the presence of a solvent or diluent, sodium sulfate hydrate is added to the final reaction solution and the resulting mixture of sodium sulfate and basic aluminum halide is filtered off. The products are known insecticides.