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The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 17 (2012) pp 125-127
DOI 10.1007/s00897122429a

A Green Multi-component Synthesis in Organic Chemistry Laboratory: A Hantzsch Dihydropyridine Synthesis and Oxidation to the Corresponding Pyridine

Kevin M. Bucholtz*, Jeffrey D. Hugdahl, Adam M. Kiefer, Kelly M. Kiefer, Amanda M. Santa Maria

Department of Chemistry, Mercer University, 1400 Coleman Avenue, Macon, GA 31207,
Received July 16, 2011. Accepted January 28, 2012.

Published: 15 June 2012

Abstract. A green and efficient synthesis of 3,5-diacetyl-1,4-dihydro-2,6-dimethylpyridine (a 1,4-dihydropyridine) and oxidation to 3,5-diacetyl-2,6-dimethylpyridine has been developed and implemented into a sophomore level organic chemistry laboratory course. The multi-component Hantzsch synthesis of formaldehyde, 2,4-pentanedione and ammonium acetate in water provides the corresponding 1,4-dihydropyridine in high yields after recrystallization from ethanol. Oxidative aromatization of the 1,4-dihydropyridine with hydrogen peroxide in the presence of catalytic amounts of iron(III) acetylacetonate generates the corresponding substituted pyridine. The products are characterized by 1H NMR, IR, and melting point.

Key Words: Laboratories and Demonstrations; organic chemistry; aqueous solution chemistry; green chemistry; synthesis

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