Multistep Microwave-Assisted Synthesis of Avobenzone

Autor/inn/en	Jordan, Annalisa M.; Wilke, Ashley E.; Nguyen, Tanifa L.; Capistrant, Katelyn C.; Zarbock, Katie R.; Batiste Simms, Morgan E.; Winsor, Brandi R.; Wollack, James W.
Titel	Multistep Microwave-Assisted Synthesis of Avobenzone
Quelle	In: Journal of Chemical Education, 99 (2022) 3, S.1435-1440 (6 Seiten)Infoseite zur Zeitschrift PDF als Volltext Verfügbarkeit
Zusatzinformation	ORCID (Wollack, James W.)
Sprache	englisch
Dokumenttyp	gedruckt; online; Zeitschriftenaufsatz
ISSN	0021-9584
DOI	10.1021/acs.jchemed.1c00818
Schlagwörter	Organic Chemistry; Science Instruction; Laboratory Experiments; Hands on Science; Radiation; College Science; Science Experiments + Suchen Sie Ihr Suchwort? Organische Chemie; Teaching of science; Science education; Natural sciences Lessons; Naturwissenschaftlicher Unterricht; Laboratory work; Laborarbeit; Strahlung
Abstract	Multistep synthesis is a key capstone experience in organic laboratory instruction. Here, a four-step synthesis of avobenzone, an active component in sunscreens, has been developed that can be completed in two 4 h laboratory periods. This synthesis incorporates green principles and includes an aldol condensation, electrophilic addition of bromine to an alkene, an E2 dehalogenation of a dibromide, and hydration of an alkyne. Highlights of this synthesis include the use of coupling constants to identify alkene configuration, NMR analysis to determine preferred tautomeric form, the use of microwave irradiation to reduce reaction times, a solvent-free synthesis of a chalcone, and a three-step reaction that can be completed in a single lab period. (As Provided).
Anmerkungen	Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Erfasst von	ERIC (Education Resources Information Center), Washington, DC
Update	2024/1/01