Eike B. Bauer
Final Abstract for URS Program
Etherification of Propargylic Alcohol using Ferrocenium Ions
Cody Amann, Sai Anvesh Bezawada and Eike B. Bauer*
Department of Chemistry and Biochemistry, University of Missouri-St.Louis, MO 63121
Our research efforts are directed toward the improvement of iron-based catalyst systems. The Bauer research group recently found that the ferrocenium cation is a catalytically active in the etherification of propargylic alcohols. My research was to compare the effect of two different counteranions of the ferrocenium cation on the catalytic activity. Etherification test reactions were performed using 2-methyl-2-phenol-propargylic alcohol and n-butanol to afford the corresponding propargylic ether substitution products. The complexes used as catalysts were ferrocenium hexafluorophosphate (I) and ferrocenium tetrafluoroborate (II) depicted below.
Test reactions shown below were performed using equimolar amounts of a propargylic alcohol and the primary n-butanol alcohol in CH2Cl2 at 40 °C with an increasing amount of catalyst load. The formation of the propargylic ether product was analyzed by using gas chromatography in 2 h and 18 h intervals. We observed an increase in the ether formation with increasing catalyst load. The research assists with increasing the efficiency of the catalyst system for the title reaction, which overall saves energy and resources in potential industrial applications.