Inventors:
Haihong Jin - Glastonbury CT
Joseph A. Feiccabrino - Naugatuck CT
Assignee:
CK Witco Corporation - Middlebury CT
International Classification:
C07C26904
C07C23102
Abstract:
Disclosed herein is a method for making compounds having the structural formulae (I) or (II): ##STR1## wherein: X is a) phenyl; lower phenylalkoxy; phenoxy; or benzyl; or b) one substituent from group a) and one or more substituents selected from C. sub. 1 -C. sub. 4 alkoxy; hydroxyl; halogen; lower alkyl; and lower alkylthio; or c) along with the phenyl to which it is attached, forms a multiple fused ring heterocycle such as dibenzofuranyl; Y is H, C. sub. 1 -C. sub. 4 alkanoyl, C. sub. 1 -C. sub. 4 haloalkanoyl dialkoxyphosphoryl, alkylaminocarbonyl, haloalkylsulfonyl, or C. sub. 1 -C. sub. 4 alkoxy carbonyl; and R is H, C. sub. 1 -C. sub. 6 alkyl, C. sub. 1 -C. sub. 6 alkoxy, C. sub. 3 -C. sub. 6 cycloalkoxy, haloalkyl, alkoxyalkyl, arylalkoxy, alkenyl, alkylthio, alkoxycarbonyl, alkylamino, heteroaryl, arylalkyl, haloalkoxy, aryloxy, or C. sub. 3 -C. sub. 6 cycloalkyl; and Z is O or S, wherein the process comprises the steps of: A) selecting as a starting material a compound of the structural formula ##STR2## B) reacting compound III with sodium nitrite in the presence of HCl to form the diazonium salt IV ##STR3## C) adding compound IV to freshly prepared alkali metal sulfite prepared by purging sulfur dioxide into an alkali metal hydroxide until the pH is between 7. 3 and 7.