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Synthesis and Analysis of a Versatile Imine for the Undergraduate Organic Chemistry Laboratory

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Jacqueline Bennett , Kristen Meldi and Christopher Kimmell II

Walter H. Hoffman Department of Chemistry, Drury University, Springfield , MO 65802

J. Chem. Educ., 2006, 83 (8), p 1221

DOI: 10.1021/ed083p1221

Publication Date (Web): August 1, 2006

Section:

History, Education, and Documentation

Abstract

An important synthesis omitted from organic laboratory texts is that of imine preparation, a particularly relevant intermediate both synthetically and biologically. In this experiment students prepare and analyze N-p-methoxyphenyl (N-PMP) α-imino ethyl glyoxalate, an imine that has been used in the synthesis of biologically active molecules. In the first step, an ethyl acetate solution of p-anisidine and ethyl glyoxalate is reacted in the presence of molecular sieves at room temperature for 15 minutes or one week. The adapted literature technique used methylene chloride as the solvent, but ethyl acetate was an equally effective "greener" alternative. Students then vacuum distill the Celite-filtered reaction mixture to remove solvent. The imine product can then be analyzed by standard organic instrumental techniques, such as ¹H NMR and GC–MS. The workup and analysis take 2–3 hours to complete, depending on instrument availability. Thus, the entire experiment can either be completed in one or two laboratory sessions. Furthermore, students compare their data to the primary literature and spectral databases, a practice seldom employed at this level. Students analyze their data for the presence of starting materials and percent conversion and discuss what this information means in their reports. The spectral signatures of the starting materials and products do not overlap, thereby simplifying the interpretation. This reaction is easy to carry out and yields a high amount of high purity product that is stable at room temperature for several weeks. The stability and versatility of this imine allow it to be used in subsequent reactions, offering a variety of possible multistep synthetic strategies.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Communication / Writing

Keywords (Subject):

Aldehydes / Ketones

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