Preparation of monoalkyl ethers of hydroxyphenols

US4383126A · kind A · utility

Assignee

• BAYER HEALTHCARE LLC · DE

Inventors

• Gerhard Buttner
• Artur Judat · Langenfeld, DE
• Udo Allenbach · Cologne, DE
• Manfred Lenthe · Odenthal, DE

Key dates

• Filing date: Oct 26, 1981
• Grant date: May 10, 1983
• Expiry date: Oct 26, 2001

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C41/16
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for the preparation of a monoalkyl ether of a hydroxyphenol of the formula ##STR1## in which Z each independently is hydrogen or a substituent which is stable under the reaction conditions, PA0 R is lower alkyl, and PA0 n is 1, 2, 3 or 4, comprising reacting a hydroxyphenol of the formula ##STR2## with an alkyl halide, alkyl sulphonate or aryl sulphonate alkylating agent of the formula EQU R--X in which X is a halogen atom, or an alkylsulphonyloxy or arylsulphonyloxy radical, at a temperature from about 130.degree. C. to 200.degree. C. and in the presence of an alkali metal base or alkaline earth metal base and of a diluent comprising a polyhydroxyalkyl ether having at least one OH group. Advantageously the base is sodium carbonate, sodium bicarbonate, potassium carbonate or potassium bicarbonate, the hydroxyphenol is pyrocatechol, the alkylating agent is isopropyl chloride, isopropyl C.sub.1-4 -alkyl-1-sulphonate, isopropyl benzenesulphonate or isopropyl tolyenesulphonate, and the polyhydroxyalkyl ether is glycol monomethyl ether, about 1.5 to 1.8 mols of alkylating agent and about 1 to 2 mols of the base being employed per mol of pyrocatechol, about 1.5 to 2.5 parts by …