Collect. Czech. Chem. Commun. 1993, 58, 1798-1802

Catalyzed Alkaline Hydrolysis of Substituted Phenyl Acetates

Jiří Kulič and Aleš Ptáček

Department of Organic Technology, University of Chemical Technology, 532 10 Pardubice, Czech Republic


2-Iodosobenzoic acid forming strong nucleophile in alkaline medium - 1-oxido-1,2-benziodoxol-3(1H)-one, was used as a catalyst of alkaline hydrolysis of substituted phenyl acetates (4-NO2, 3-NO2, 3-Cl, 4-Br, H, 4-CH3, 3-CH3, 4-OCH3, 3-OCH3) in the presence of hexadecyltrimethylammonium bromide as a micellar agent. It was found that the observed first-order rate constants kobs can be correlated by the Hammett equation: log kobs = (-3.29 ± 0.03) + (1.77 ± 0.001) σ.