BF3-H2O catalyzed Fries rearrangement of phenolic esters

ORGN 830

G. K. Surya Prakash, gprakash@usc.edu, Chiradeep Panja, chiradep@usc.edu, Thomas Mathew, tmathew@usc.edu, and George A. Olah, olah@usc.edu. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661
Hydroxyarylketones are synthetically and industrially important compounds. Many of them are used in perfumes, pharmaceuticals, paints and varnishes, metallurgy, plastics, films and natural and synthetic rubber industry. Several methods such as Friedel-Crafts reaction, Hoesch and Nencki reaction, Fries reaction etc. are available for the preparation of hydroxyaryl ketones. Among these, the Fries rearrangement is the most widely employed method. During the course of our study with BF3-H2O, we found that it can be used as a strong Brønsted acid system for Fries rearrangement. Aromatic and alkyl carboxylic acid esters of phenols react equally well to produce the corresponding hydroxy ketones in good to excellent chemical yields with high para selectivity. Simplicity, clean reaction, use of inexpensive acid, solvent free conditions and lack of elaborate purification processes, make the presently developed Fries reaction more useful, economic and environmentally desirable.

 

Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007