Aromatic halogenation is an important tool for the conversion of aromatic compounds into specific compounds of interest or importance. This laboratory module investigates the iodination of 4'-hydroxyacetophenone using sodium iodine and household bleach (as an oxidizing agent) in aqueous ethanol. The reaction conditions used in this laboratory module offer two advantages over more traditional methods: (1) the reaction is efficient and selective leading to good yields of monoiodinated product and (2) the method offers more environmentally benign reaction conditions (less hazardous oxidizing agent - NaOCl vs. nitric acid and a relative benign solvent- ethanol). The link to the laboratory procedures includes pre- and -post lab questions.
Summary prepared May 2005 by Julie A. Haack, Department of Chemistry at the University of Oregon.
Gilbertson, R.; Parent, K. E.; McKenzie, L. C.; Hutchison, J. E. Electrophilic Aromatic Iodination of 4'-Hydroxyacetophenone Greener Approaches to Undergraduate Chemistry Experiments, Print Kirchhoff, M., Ryan, M., Eds.; American Chemical Society: Washington D.C., 2002; pp 1-3.