Multistep Microwave-Assisted Synthesis of Avobenzone

• Annalisa M. Jordan ^[1] ; Ashley E. Wilke ^[1] ; Tanifa L. Nguyen ^[1] ; Katelyn C. Capistrant ^[1] ; Katie R. Zarbock ^[1] ; Morgan E. Batiste Simms ^[1] ; Brandi R. Winsor ^[1] ; James W. Wollack ^[1]
  1. [1] St. Catherine University

     St. Catherine University

     City of Saint Paul, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 99, Nº 3, 2022, págs. 1435-1440
• Idioma: inglés
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• Resumen

  • 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.