Multistep Microwave-Assisted Synthesis of Avobenzone

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...

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Bibliographic Details
Published in:Journal of chemical education 2022-03, Vol.99 (3), p.1435-1440
Main Authors: 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
Format: Article
Language:English
Subjects:
Aldehydes
Alkynes
Bromine
Chemical synthesis
College Science
Condensation
Hands on Science
Irradiation
Laboratory Experiments
NMR
Nuclear magnetic resonance
Organic Chemistry
Radiation
Reaction time
Science Experiments
Science Instruction
Sun screens
Sunscreen
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Summary: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.
ISSN:0021-9584
1938-1328
DOI:10.1021/acs.jchemed.1c00818