MANUFACTURE OF 3-(ACYL)AMINO-4-ALKOXYPHENYL-BETA- HYDROXYETHYLSULFONE(-SULFURIC ACID ESTER)

摘要

A process for the preparation of 3-(acyl)amino-4-alkoxy-phenyl- beta -hydroxyethyl-sulfone (sulfates) of the formula (1) IMAGE (1) in which R1 is alkyl having 1-4 carbon atoms and R2 is hydrogen or one of the groupings IMAGE IMAGE IMAGE +TR IMAGE with the proviso that n=1 if R2=H and n=0 if R2=acyl, by converting 2-alkoxyacylanilines of the formula (2) IMAGE (2) in which R1 and R2 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 DEG C. to give the corresponding sulfinates, alkoxylating the latter with ethylene oxide in an aqueous medium at pH 6.0-8.5 and 40 DEG -80 DEG C. to give the 3-acylamino-4-alkoxyphenyl- beta -hydroxyethyl-sulfones of the formula (1) (with R2=acyl and n=0) and, if appropriate, esterifying the latter, with deacylation, with concentrated sulfuric acid at 70 DEG -150 DEG C. to give the compounds of the said formula (1) (with R2H and n=1).