Process for the preparation of halogenated hydroxydiphenyl compounds

US6706930B2 · kind B2 · utility

Assignee

• Ciba Specialty Chemicals Corporation · US

Inventors

• Armando Di Teodoro · Rheinfelden (Baden), DE
• Werner Hölzl · Eschentzwiller, FR
• Dieter Reinehr · Kandern, DE
• Rudolf Zink · Therwil, CH

Key dates

• Filing date: Oct 31, 2002
• Grant date: Mar 16, 2004
• Expiry date: Oct 31, 2022

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C45/71
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

There is described a process for the preparation of halogenated hydroxydiphenyl compounds of formula (1) by acylation of a halogenated benzene compound (first stage), etherification of the acylated compound with a halogenated phenol compound, which is not further substituted in the ortho-position (second stage), oxidation of the etherified compound (third stage) and hydrolysis of the oxidized compound in a fourth stage, wherein the reaction of the second stage is carried out in the presence of K2CO3 and any desired copper catalyst, where K2CO3 is used in a concentration of from 0.5 to 30 mol, based on the phenol compound employed of formula (6), according to the reaction scheme (I) in which R1 and R2 independently of one another are F, Cl or Br; R3 and R4 independently of one another are hydrogen; or C1-C4alkyl; m is 1 to 3; and n is 1 or 2. The compounds of formula (1) are used for protecting organic materials and articles from microorganisms.