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Convenient Microscale Synthesis of a Coumarin Laser Dye Analog

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Evangelos Aktoudianakis and Andrew P. Dicks

Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada

J. Chem. Educ., 2006, 83 (2), p 287

DOI: 10.1021/ed083p287

Publication Date (Web): February 1, 2006

Section:

History, Education, and Documentation

Abstract

The expeditious Knoevenagel synthesis of 3-acetyl-7-(diethylamino)-2H-1-benzopyran-2-one, a fluorescent coumarin laser dye analog, is described. This experiment is suitable for inclusion in mid-level undergraduate organic chemistry laboratories. The synthesis highlights the efficiency, safety, and time effectiveness of microscale chemistry while stressing fundamental reaction mechanisms and analytical techniques to students. The coumarin product affords informative proton NMR, infrared, UV–visible, and fluorescence spectra that introduce and reinforce essential concepts such as molecular light absorption and emission.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Aromatic Compounds

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