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Fries Rearrangement Accelerated by Microwave Radiation in the Undergraduate Organic Laboratory
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Abstract
Herein we present an opportunity for undergraduate students to carry out a reaction using microwave radiation. The rapid rate of reaction prevents student boredom and inactivity. The rate increase appears to be due primarily to rapid attainment of high reaction temperatures. However, the possibility of an additional modest acceleration in rate due to some effect specific to the microwave wavelengths employed has not been completely excluded.
We have found that the Fries rearrangement of aryl esters to ortho- and para-hydroxy acetophenones can be carried out in dry open media in ordinary glassware using a commercial microwave oven. The Fries rearrangement normally requires a Lewis acid and long reflux times or photochemical conditions.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
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This article has been cited by 7 ACS Journal articles (5 most recent appear below).
Microwave-Enhanced Organic Syntheses for the Undergraduate Laboratory: Diels−Alder Cycloaddition, Wittig Reaction, and Williamson Ether Synthesis
Marsha R. Baar, Danielle Falcone and Christopher GordonJournal of Chemical Education2010 87 (1), 84-86Microwave-Enhanced Organic Syntheses for the Undergraduate Laboratory: Diels−Alder Cycloaddition, Wittig Reaction, and Williamson Ether Synthesis
Marsha R. Baar, Danielle Falcone and Christopher GordonJournal of Chemical Education2010 87 (1), 84-86Microwave heating enhanced the rate of three reactions typically performed in our undergraduate organic chemistry laboratory: a Diels−Alder cycloaddition, a Wittig salt formation, and a Williamson ether synthesis. Ninety-minute refluxes were shortened to ...
Microwave-Assisted Carbonyl Chemistry for the Undergraduate Laboratory
C. Oliver Kappe , S. Shaun MurphreeJournal of Chemical Education2009 86 (2), 227Microwave-Assisted Carbonyl Chemistry for the Undergraduate Laboratory
C. Oliver Kappe , S. Shaun MurphreeJournal of Chemical Education2009 86 (2), 227An instructional laboratory module suitable for a second- or third-year organic chemistry curriculum has been developed using microwave-assisted synthetic techniques. The module, which contains six discrete experiments, explores various aspects of ...
Microwave-Assisted Organic Synthesis in the Organic Teaching Lab: A Simple, Greener Wittig Reaction
Eric Martin and Cynthia Kellen-YuenJournal of Chemical Education2007 84 (12), 2004Microwave-Assisted Organic Synthesis in the Organic Teaching Lab: A Simple, Greener Wittig Reaction
Eric Martin and Cynthia Kellen-YuenJournal of Chemical Education2007 84 (12), 2004A greener, microwave-assisted Wittig reaction has been developed for the second-semester organic teaching laboratory. Utilizing this microwave technique, a variety of styrene derivatives have been successfully synthesized from aromatic aldehydes in good ...
Incorporation of Microwave Synthesis into the Undergraduate Organic Laboratory
E. Keller Barnhardt , Alan R. Katritzky , Chunming Cai , Meghan D. Collins , Eric F. V. Scriven and Sandeep K. SinghJournal of Chemical Education2006 83 (4), 634Incorporation of Microwave Synthesis into the Undergraduate Organic Laboratory
E. Keller Barnhardt , Alan R. Katritzky , Chunming Cai , Meghan D. Collins , Eric F. V. Scriven and Sandeep K. SinghJournal of Chemical Education2006 83 (4), 634As the acceptance of microwave synthesis grows, it becomes increasingly important for undergraduate chemists to fully learn about this emerging technology. Advances have made microwave use in the undergraduate laboratory safe, easy, and affordable. Herein ...
Functional Group Transformations of Diols, Cyclic Ethers, and Lactones Using Aqueous Hydrobromic Acid and Phase Transfer Catalyst under Microwave Irradiation
Goverdhan L. Kad, Irvinder Kaur, Monica Bhandari, Jasvinder Singh, and Jasamrit KaurOrganic Process Research & Development2003 7 (3), 339-340Functional Group Transformations of Diols, Cyclic Ethers, and Lactones Using Aqueous Hydrobromic Acid and Phase Transfer Catalyst under Microwave Irradiation
Goverdhan L. Kad, Irvinder Kaur, Monica Bhandari, Jasvinder Singh, and Jasamrit KaurOrganic Process Research & Development2003 7 (3), 339-340Synthesis of bromoalkanols has been achieved from diols, ethers, and lactones using aq HBr (48%) and tetrabutylammonium iodide/bromide as phase transfer catalyst under microwave irradiation. This environmentally benign route provides enhanced yields of ...
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- Received: August 03, 2009
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