The Chemical Educator
ISSN: 1430-4171 (electronic version)
Abstract Volume 17
(2012) pp 125-127
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
Avenue, Macon, GA 31207, email@example.com
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
(*) Corresponding author. (E-mail: firstname.lastname@example.org)
Supporting Materials:One supporting file is available containing student directions and instructor’s notes (159 KB).