Preparation and properties of chlorinated syringic acids, acetosyringones, acetoguaiacones and methoxy-p-hydroquinones — components of pulp bleaching effluents

A range of chlorinated phenols which serve as standards for compounds occurring in effluents from the bleaching of wood pulps with chlorine-containing reagents has been prepared. The chlorinated phenols include chlorosyringic acids, chloroacetosyringones, chloroacetoguaiacones, 5-chloro-2-methoxy-p-hydroquinone and chloro-2,6-dimethoxy-p-hydroquinones. With the exception of the ring-chlorinated acetoguaiacones which were prepared by reaction of chlorovanillin acetates with diazomethane, the compounds were obtained by direct chlorination of appropriate phenols or their acetates. Gas chromatographic and mass spectrometric data for the acetylated phenols are given.