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In the Laboratory
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Grubbs's Cross Metathesis of Eugenol with cis-2-Butene-1,4-diol To Make a Natural Product. An Organometallic Experiment for the Undergraduate Lab
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Douglass F. Taber and Kevin J. Frankowski
Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716
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February 2006
Vol. 83 No. 2
p. 283
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| Abstract |
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An experiment for the undergraduate organic laboratory course, the ruthenium catalyzed cross metathesis of eugenol with cis-1,4-butenediol, is described in detail. The Grubbs' catalyst is dispersed in paraffin wax to eliminate the need for inert atmosphere storage. Eugenol, the main component of clove oil, is coupled at room temperature overnight with cis-1,4-butenediol to yield the crystalline (E)-4-(4-hydroxy-3-methoxyphenyl)but-2-en-ol, also a natural product. The experiment is an excellent example of the powerful selectivity possible with the Grubbs' catalyst. Both the preference for trans over cis alkene formation and for cross metathesis over homodimerization are demonstrated. The experiment also provides an opportunity for students to gain proficiency in the organic synthesis techniques of column chromatography, TLC, recrystallization, and melting point determination. Optional characterization of the product by IR, mass spec, and 1H NMR make the experiment applicable for all levels of undergraduate organic students.
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| Supplement |
A student handout containing a step-by-step procedure, notes for the instructor, 1H, 13C NMR, IR spectra, and the electron impact mass spectrum are available.
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| More Information |
Citation |
Taber, Douglass F.; Frankowski, Kevin J. J. Chem. Educ. 2006 83 283.
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Keywords |
Alkenes; Catalysis; Hands-On Learning / Manipulatives; IR Spectroscopy; Laboratory Instruction; Mass Spectrometry; Mechanisms of Reactions; Microscale Lab; Natural Products; NMR Spectroscopy; Organic Chemistry; Organometallics; Second-Year Undergraduate; Stereochemistry; Synthesis; Thin Layer Chromatography; Transition Elements
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History |
Created:
Last Updated: |
1/5/2006
1/10/2006
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| Home > JCE Print > Journal of Chemical Education > Issues >
2006
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February
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283
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