ORGN 478 |
| The development of a simple, cost-efficient, and environmentally friendly Lewis acid-catalyzed reaction of structurally diverse compounds is under active investigation. This catalytic version can prevent unwanted side reactions such as dimerization and polymerization. The major improvement from our laboratory is to use bismuth derived catalysts. We have been studying environmentally friendly reactions mediated by metals or their salts with the aim of developing several biologically active compounds, including several anticancer agents and â-lactams. Acetylsalicylic acid, commonly known as aspirin, is used as a mild anti-inflammatory analgesic. Commercial aspirin is synthesized through an acylation reaction of salicylic acid and acetic anhydride in strong acidic medium. Friedel-Crafts acylation is a widely used method both in the laboratory and industry for the production of aryl ketones, including aspirin via electrophilic substitution. The reaction involves the use of acid chlorides or acid anhydride with addition of stoichiometric quantities of acid or excess alkali. The disadvantages of these methods have prompted interest in the development of a catalytic process that can occur under mild and environmentally friendly conditions. This study will investigate the effectiveness of bismuth nitrate and other related catalysts in the reaction of salicylic acid with acetic anhydride to produce acetylsalicylic acid. The commercial availability of bismuth nitrate and its nontoxic, oxygen and moisture tolerant properties makes it a most suitable catalyst. This project is supported through a HHMI grant.
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New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |