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  Home > JCE Print > Journal of Chemical Education > Issues > 2001  > April  >
In the Laboratory
Isolating Friedelin from Cork and Reducing It to Friedelinol and Epifriedelinol. A Project Involving NMR Spectrometry and Molecular Modeling
Joseph W. LeFevre, Kristin I. McNeill, and Janet L. Moore
Chemistry Department, State University of New York (SUNY) at Oswego, Oswego, NY 13126
Cover
April 2001
Vol. 78 No. 4
p. 535
Abstract
In this four-week project, the pentacyclic triterpene friedelin is isolated from laboratory cork. The ground cork is refluxed in ethyl acetate, from which crude friedelin crystallizes. The crude product is analyzed by thin-layer chromatography and purified by flash chromatography. The resulting pure friedelin is reduced to friedelinol and epifriedelinol using different reduction conditions. Each product is analyzed by 1H NMR spectrometry and identified by comparing the CHOH signal with the corresponding signal in the model compounds, menthol and neomenthol. Finally, from computer-generated 3-D molecular models of each alcohol, key dihedral angles are measured and used to calculate three proton-proton coupling constants (J values) involving the CHOH proton. These values are compared to the actual J values determined by NMR spectrometry.
Supplement
Supplemental materials available include a detailed student handout and Instructors' Notes, which contain comments on the experiment, lists of equipment and reagents, and answers to questions in the student handout.
*  Contents JCE2001p0535W.doc (MS Word 97-98)
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*  Citation
 LeFevre, Joseph W. ; McNeill, Kristin I.; Moore, Janet L. J. Chem. Educ. 2001 78 535.
*  Keywords
 Chromatography; Laboratory Instruction; Molecular Modeling / Dynamics; Natural Products; NMR Spectrometry; Organic Chemistry
*  History
 Created:
Last Updated:		 March 2, 2001
August 31, 2005
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