Loading…
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...
Saved in:
Published in: | Journal of chemical education 2022-03, Vol.99 (3), p.1435-1440 |
---|---|
Main Authors: | , , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
cited_by | cdi_FETCH-LOGICAL-a254t-32d17a46851804faeda733c638f852f67a1ae0358c8f844a96018fe562da79033 |
---|---|
cites | cdi_FETCH-LOGICAL-a254t-32d17a46851804faeda733c638f852f67a1ae0358c8f844a96018fe562da79033 |
container_end_page | 1440 |
container_issue | 3 |
container_start_page | 1435 |
container_title | Journal of chemical education |
container_volume | 99 |
creator | 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 |
description | 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. |
doi_str_mv | 10.1021/acs.jchemed.1c00818 |
format | article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2641934868</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><ericid>EJ1328598</ericid><sourcerecordid>2641934868</sourcerecordid><originalsourceid>FETCH-LOGICAL-a254t-32d17a46851804faeda733c638f852f67a1ae0358c8f844a96018fe562da79033</originalsourceid><addsrcrecordid>eNp9kE1PwkAQhjdGExH9BcakiefCfjM9EoJfgXhQz5t1OxtKoMXdgsFf72LRo6fJzLzvfDyEXDM6YJSzoXVxsHQLXGM5YI5SYHBCeqwQkDPB4ZT0aJLlhQJ5Ti5iXFLKuCqgR-R8u2qr2OImm1cuNJ92h_k4xkOpzF72dbvAlGSNz8a75h3rr6bGS3Lm7Sri1TH2ydvd9HXykM-e7x8n41luuZJtLnjJRlZqUAyo9BZLOxLCaQEeFPd6ZJlFKhS4VJDSFpoy8Kg0T8KCCtEnt93cTWg-thhbs2y2oU4rDdcyvSdBQ1KJTpXOjzGgN5tQrW3YG0bNAY9JeMwRjzniSa6bzoWhcn-O6dOBVyKT-sOu_2P-XfvfxG_RDnOH</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2641934868</pqid></control><display><type>article</type><title>Multistep Microwave-Assisted Synthesis of Avobenzone</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)</source><source>ERIC</source><creator>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</creator><creatorcontrib>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</creatorcontrib><description>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.</description><identifier>ISSN: 0021-9584</identifier><identifier>EISSN: 1938-1328</identifier><identifier>DOI: 10.1021/acs.jchemed.1c00818</identifier><language>eng</language><publisher>Easton: American Chemical Society and Division of Chemical Education, Inc</publisher><subject>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</subject><ispartof>Journal of chemical education, 2022-03, Vol.99 (3), p.1435-1440</ispartof><rights>2022 American Chemical Society and Division of Chemical Education, Inc.</rights><rights>Copyright American Chemical Society Mar 8, 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a254t-32d17a46851804faeda733c638f852f67a1ae0358c8f844a96018fe562da79033</citedby><cites>FETCH-LOGICAL-a254t-32d17a46851804faeda733c638f852f67a1ae0358c8f844a96018fe562da79033</cites><orcidid>0000-0003-3124-721X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids><backlink>$$Uhttp://eric.ed.gov/ERICWebPortal/detail?accno=EJ1328598$$DView record in ERIC$$Hfree_for_read</backlink></links><search><creatorcontrib>Jordan, Annalisa M</creatorcontrib><creatorcontrib>Wilke, Ashley E</creatorcontrib><creatorcontrib>Nguyen, Tanifa L</creatorcontrib><creatorcontrib>Capistrant, Katelyn C</creatorcontrib><creatorcontrib>Zarbock, Katie R</creatorcontrib><creatorcontrib>Batiste Simms, Morgan E</creatorcontrib><creatorcontrib>Winsor, Brandi R</creatorcontrib><creatorcontrib>Wollack, James W</creatorcontrib><title>Multistep Microwave-Assisted Synthesis of Avobenzone</title><title>Journal of chemical education</title><addtitle>J. Chem. Educ</addtitle><description>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.</description><subject>Aldehydes</subject><subject>Alkynes</subject><subject>Bromine</subject><subject>Chemical synthesis</subject><subject>College Science</subject><subject>Condensation</subject><subject>Hands on Science</subject><subject>Irradiation</subject><subject>Laboratory Experiments</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic Chemistry</subject><subject>Radiation</subject><subject>Reaction time</subject><subject>Science Experiments</subject><subject>Science Instruction</subject><subject>Sun screens</subject><subject>Sunscreen</subject><issn>0021-9584</issn><issn>1938-1328</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>7SW</sourceid><recordid>eNp9kE1PwkAQhjdGExH9BcakiefCfjM9EoJfgXhQz5t1OxtKoMXdgsFf72LRo6fJzLzvfDyEXDM6YJSzoXVxsHQLXGM5YI5SYHBCeqwQkDPB4ZT0aJLlhQJ5Ti5iXFLKuCqgR-R8u2qr2OImm1cuNJ92h_k4xkOpzF72dbvAlGSNz8a75h3rr6bGS3Lm7Sri1TH2ydvd9HXykM-e7x8n41luuZJtLnjJRlZqUAyo9BZLOxLCaQEeFPd6ZJlFKhS4VJDSFpoy8Kg0T8KCCtEnt93cTWg-thhbs2y2oU4rDdcyvSdBQ1KJTpXOjzGgN5tQrW3YG0bNAY9JeMwRjzniSa6bzoWhcn-O6dOBVyKT-sOu_2P-XfvfxG_RDnOH</recordid><startdate>20220308</startdate><enddate>20220308</enddate><creator>Jordan, Annalisa M</creator><creator>Wilke, Ashley E</creator><creator>Nguyen, Tanifa L</creator><creator>Capistrant, Katelyn C</creator><creator>Zarbock, Katie R</creator><creator>Batiste Simms, Morgan E</creator><creator>Winsor, Brandi R</creator><creator>Wollack, James W</creator><general>American Chemical Society and Division of Chemical Education, Inc</general><general>Division of Chemical Education, Inc</general><general>American Chemical Society</general><scope>7SW</scope><scope>BJH</scope><scope>BNH</scope><scope>BNI</scope><scope>BNJ</scope><scope>BNO</scope><scope>ERI</scope><scope>PET</scope><scope>REK</scope><scope>WWN</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><orcidid>https://orcid.org/0000-0003-3124-721X</orcidid></search><sort><creationdate>20220308</creationdate><title>Multistep Microwave-Assisted Synthesis of Avobenzone</title><author>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</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a254t-32d17a46851804faeda733c638f852f67a1ae0358c8f844a96018fe562da79033</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Aldehydes</topic><topic>Alkynes</topic><topic>Bromine</topic><topic>Chemical synthesis</topic><topic>College Science</topic><topic>Condensation</topic><topic>Hands on Science</topic><topic>Irradiation</topic><topic>Laboratory Experiments</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic Chemistry</topic><topic>Radiation</topic><topic>Reaction time</topic><topic>Science Experiments</topic><topic>Science Instruction</topic><topic>Sun screens</topic><topic>Sunscreen</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jordan, Annalisa M</creatorcontrib><creatorcontrib>Wilke, Ashley E</creatorcontrib><creatorcontrib>Nguyen, Tanifa L</creatorcontrib><creatorcontrib>Capistrant, Katelyn C</creatorcontrib><creatorcontrib>Zarbock, Katie R</creatorcontrib><creatorcontrib>Batiste Simms, Morgan E</creatorcontrib><creatorcontrib>Winsor, Brandi R</creatorcontrib><creatorcontrib>Wollack, James W</creatorcontrib><collection>ERIC</collection><collection>ERIC (Ovid)</collection><collection>ERIC</collection><collection>ERIC</collection><collection>ERIC (Legacy Platform)</collection><collection>ERIC( SilverPlatter )</collection><collection>ERIC</collection><collection>ERIC PlusText (Legacy Platform)</collection><collection>Education Resources Information Center (ERIC)</collection><collection>ERIC</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Journal of chemical education</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jordan, Annalisa M</au><au>Wilke, Ashley E</au><au>Nguyen, Tanifa L</au><au>Capistrant, Katelyn C</au><au>Zarbock, Katie R</au><au>Batiste Simms, Morgan E</au><au>Winsor, Brandi R</au><au>Wollack, James W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><ericid>EJ1328598</ericid><atitle>Multistep Microwave-Assisted Synthesis of Avobenzone</atitle><jtitle>Journal of chemical education</jtitle><addtitle>J. Chem. Educ</addtitle><date>2022-03-08</date><risdate>2022</risdate><volume>99</volume><issue>3</issue><spage>1435</spage><epage>1440</epage><pages>1435-1440</pages><issn>0021-9584</issn><eissn>1938-1328</eissn><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.</abstract><cop>Easton</cop><pub>American Chemical Society and Division of Chemical Education, Inc</pub><doi>10.1021/acs.jchemed.1c00818</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-3124-721X</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0021-9584 |
ispartof | Journal of chemical education, 2022-03, Vol.99 (3), p.1435-1440 |
issn | 0021-9584 1938-1328 |
language | eng |
recordid | cdi_proquest_journals_2641934868 |
source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list); ERIC |
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 |
title | Multistep Microwave-Assisted Synthesis of Avobenzone |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-09-22T18%3A31%3A37IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Multistep%20Microwave-Assisted%20Synthesis%20of%20Avobenzone&rft.jtitle=Journal%20of%20chemical%20education&rft.au=Jordan,%20Annalisa%20M&rft.date=2022-03-08&rft.volume=99&rft.issue=3&rft.spage=1435&rft.epage=1440&rft.pages=1435-1440&rft.issn=0021-9584&rft.eissn=1938-1328&rft_id=info:doi/10.1021/acs.jchemed.1c00818&rft_dat=%3Cproquest_cross%3E2641934868%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a254t-32d17a46851804faeda733c638f852f67a1ae0358c8f844a96018fe562da79033%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2641934868&rft_id=info:pmid/&rft_ericid=EJ1328598&rfr_iscdi=true |