Process for preparation of 3-(acyl)amino-4-alkoxy-phenyl-.beta.-hydroxyethyl-sulfone (sulfonates)

US4778911A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Peter Hess
• Folker Kohlhaas · Hochheim, DE
• Theodor Papenfuhs · Frankfurt, DE

Key dates

• Filing date: Jun 18, 1987
• Grant date: Oct 18, 1988
• Expiry date: Jun 18, 2007

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C315/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for the preparation of 3-(acyl)amino-4-alkoxy-phenyl-.beta.-hydroxyethyl-sulfone (sulfates) of the formula (1) ##STR1## in which R.sub.1 is alkyl having 1-4 carbon atoms and R.sub.2 is hydrogen or one of the groupings ##STR2## with the proviso that n=1 if R.sub.2 =H and n=0 if R.sub.2 =acyl, by converting 2-alkoxyacylanilines of the formula (2) ##STR3## in which R.sub.1 and R.sub.2 have the meanings given, in a known manner to the corresponding sulfochlorides substituted in the p-position relative to the alkoxy group, reducing the sulfochlorides with an alkali metal sulfite or ammonium sulfite in an aqueous medium at pH 7.0-8.5 and at -5 to +40.degree. C. to give the corresponding sulfinates, alkoxylating the latter with ethylene oxide in an aqueous medium at pH 6.0-8.5 and 40.degree.-80.degree. C. to give the 3-acylamino-4-alkoxyphenyl-.beta.-hydroxyethyl-sulfones of the formula (1) (with R.sub.2 =acyl and n=0) and, if appropriate, esterifying the latter, with deacylation, with concentrated sulfuric acid at 70.degree.-150.degree. C. to give the compounds of the said formula (1) (with R.sub.2 H and n=1).