6344-28-1Relevant articles and documents
The α-chlorination of aryl methyl ketones under aerobic oxidative conditions
Prebil, Rok,Stavber, Stojan
supporting information, p. 1266 - 1274 (2014/05/06)
The novel reaction system air/ammonium nitrate/iodine/hydrochloric acid [air/NH4NO3(cat.)/I2(cat.)/HCl] is introduced as a simple, safe, cheap, efficient and regioselective mediator for the α-chlorination of aryl, heteroaryl and alkyl methyl ketones under aerobic oxidative conditions. The inventive use of a catalytic amount of iodine enabled the moderate to quantitative, regioselective chlorination of a comprehensive scope of different methyl ketone derivatives including those bearing oxidizable heteroatom (S, N) substituents, some of which possess declared potential biological and pharmaceutical activity. Air oxygen under a slight overpressure plays the role of the terminal oxidant catalytically activated by redox cycles of nitrogen oxides released from the catalytic amount of ammonium nitrate (NH4NO3) under acidic conditions of hydrochloric acid (HCl) and co-catalyzed by elemental iodine (I2), which was found to be essential for the high efficiency of the reaction system.
Preparation and properties of chlorinated syringic acids, acetosyringones, acetoguaiacones and methoxy-p-hydroquinones components of pulp bleaching effluents
Smith,Wearne,Wallis
, p. 69 - 80 (2007/10/03)
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.