The Chemical EducatorISSN: 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 PyridineKevin 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, bucholtz_km@mercer.edu 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: bucholtz_km@mercer.edu) Article in PDF format (164 KB) HTML format Supporting Materials: One supporting file is available containing student directions and instructor’s notes (159 KB).
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