Friedel-Crafts acylations of cycloalkylbenzene: Acylation vs. intermolecular cycloalkane migration

CHED 303

Amanda E. Conway, amanda.conway@villanova.edu1, Christine Clark, christine.clark@villanova.edu1, Amy Styer1, Gianmarc Johns, gianmarc.johns@villanova.edu1, and Barry S. Selinsky, barry.selinsky@villanova.edu2. (1) Chemistry Department, Villanova University, 800 Lancaster Ave., Villanova, PA 19085, (2) Department of Chemistry, Villanova University, 800 Lancaster Avenue, Villanova, PA 19085
Friedel-Crafts acylations were first documented in 1877 and are important in the synthesis of substituted aromatic compounds. While pursuing the synthesis of non-steroidal anti-inflammatory agents, we observed multiple products in an attempted synthesis of 1-(4-cyclohexyl-phenyl)propan-1-one. The reaction of cyclohexyl benzene with propionyl chloride in CH2Cl2, using AlCl3 as a catalyst, generated both the expected phenyl propanone and an unexpected 1-(2,4-dicyclohexyl-phenyl)propan-1-one. The source of the unexpected product and a mechanism for its formation are presented, referring to earlier studies on the aluminum chloride catalyzed isomerizations of alkylbenzenes.
 

Undergraduate Research Poster Session: Organic Chemistry
2:30 PM-4:30 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Poster

Division of Chemical Education

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006