Selective para metalation of unprotected 3-methoxy and 3,5-dimethoxy benzoic acids with n- butyl lithium–potassium tert -butoxide (LIC–KOR): synthesis of 3,5-dimethoxy-4-methyl benzoic acid
Identifieur interne : 001317 ( Istex/Corpus ); précédent : 001316; suivant : 001318Selective para metalation of unprotected 3-methoxy and 3,5-dimethoxy benzoic acids with n- butyl lithium–potassium tert -butoxide (LIC–KOR): synthesis of 3,5-dimethoxy-4-methyl benzoic acid
Auteurs : Surajit Sinha ; Bhubaneswar Mandal ; Srinivasan ChandrasekaranSource :
- Tetrahedron Letters [ 0040-4039 ] ; 2000.
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Abstract
Abstract: The potassium salt of 3-methoxy and 3,5-dimethoxy benzoic acids undergoes deprotonation at the position para to the carboxylate group selectively when treated with LIC–KOR in THF at −78°C and it has been extended to the synthesis of 3,5-dimethoxy-4-methyl benzoic acid.
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DOI: 10.1016/S0040-4039(00)00320-8
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3,5-dimethoxy-4-methyl benzoic acid</title><author><name sortKey="Sinha, Surajit" sort="Sinha, Surajit" uniqKey="Sinha S" first="Surajit" last="Sinha">Surajit Sinha</name><affiliation><mods:affiliation>Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India</mods:affiliation></affiliation></author><author><name sortKey="Mandal, Bhubaneswar" sort="Mandal, Bhubaneswar" uniqKey="Mandal B" first="Bhubaneswar" last="Mandal">Bhubaneswar Mandal</name><affiliation><mods:affiliation>Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India</mods:affiliation></affiliation></author><author><name sortKey="Chandrasekaran, Srinivasan" sort="Chandrasekaran, Srinivasan" uniqKey="Chandrasekaran S" first="Srinivasan" last="Chandrasekaran">Srinivasan Chandrasekaran</name><affiliation><mods:affiliation>Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, 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iodide</term><term>Mmol</term><term>Ortho</term><term>Para</term><term>Perkin trans</term><term>Potassium salt</term><term>Schlosser</term><term>Super base</term><term>Tetrahedron</term><term>Tetrahedron lett</term><term>alkylation</term><term>carboxylic acids</term><term>metalation</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Benzoic</term><term>Benzoic acid</term><term>Carboxylic</term><term>Carboxylic acid</term><term>Cdcl3</term><term>Chem</term><term>Equiv</term><term>Ester</term><term>Lett</term><term>Metalation</term><term>Methyl</term><term>Methyl ester</term><term>Methyl iodide</term><term>Mmol</term><term>Ortho</term><term>Para</term><term>Perkin trans</term><term>Potassium salt</term><term>Schlosser</term><term>Super base</term><term>Tetrahedron</term><term>Tetrahedron lett</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: The potassium salt of 3-methoxy and 3,5-dimethoxy benzoic acids undergoes deprotonation at the position para to the carboxylate group selectively when treated with LIC–KOR in THF at −78°C and it has been extended to the synthesis of 3,5-dimethoxy-4-methyl benzoic acid.</div></front></TEI><istex><corpusName>elsevier</corpusName><keywords><teeft><json:string>benzoic</json:string><json:string>benzoic acid</json:string><json:string>chem</json:string><json:string>carboxylic</json:string><json:string>tetrahedron</json:string><json:string>para</json:string><json:string>equiv</json:string><json:string>metalation</json:string><json:string>lett</json:string><json:string>tetrahedron lett</json:string><json:string>methyl iodide</json:string><json:string>ester</json:string><json:string>potassium salt</json:string><json:string>cdcl3</json:string><json:string>ortho</json:string><json:string>mmol</json:string><json:string>schlosser</json:string><json:string>methyl ester</json:string><json:string>carboxylic 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xml:lang="en">Selective para metalation of unprotected 3-methoxy and 3,5-dimethoxy benzoic acids with n- butyl lithium–potassium tert -butoxide (LIC–KOR): synthesis of 3,5-dimethoxy-4-methyl benzoic acid</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>ELSEVIER</publisher><availability><p>©2000 Elsevier Science Ltd</p></availability><date>2000</date></publicationStmt><notesStmt><note type="content">Table 1:</note></notesStmt><sourceDesc><biblStruct type="inbook"><analytic><title level="a" type="main" xml:lang="en">Selective para metalation of unprotected 3-methoxy and 3,5-dimethoxy benzoic acids with n- butyl lithium–potassium tert -butoxide (LIC–KOR): synthesis of 3,5-dimethoxy-4-methyl benzoic acid</title><author xml:id="author-0000"><persName><forename type="first">Surajit</forename><surname>Sinha</surname></persName><affiliation>Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India</affiliation></author><author xml:id="author-0001"><persName><forename type="first">Bhubaneswar</forename><surname>Mandal</surname></persName><affiliation>Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India</affiliation></author><author xml:id="author-0002"><persName><forename type="first">Srinivasan</forename><surname>Chandrasekaran</surname></persName><note type="correspondence"><p>Corresponding author</p></note><affiliation>Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India</affiliation></author><idno type="istex">6595B27F5E97E6060193E0D50BD6F4D9542CDDA4</idno><idno type="DOI">10.1016/S0040-4039(00)00320-8</idno><idno type="PII">S0040-4039(00)00320-8</idno></analytic><monogr><title level="j">Tetrahedron Letters</title><title level="j" type="abbrev">TETL</title><idno type="pISSN">0040-4039</idno><idno type="PII">S0040-4039(00)X0254-7</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="2000"></date><biblScope unit="volume">41</biblScope><biblScope unit="issue">17</biblScope><biblScope unit="page" from="3157">3157</biblScope><biblScope unit="page" to="3160">3160</biblScope></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>2000</date></creation><langUsage><language ident="en">en</language></langUsage><abstract xml:lang="en"><p>The potassium salt of 3-methoxy and 3,5-dimethoxy benzoic acids undergoes deprotonation at the position para to the carboxylate group selectively when treated with LIC–KOR in THF at −78°C and it has been extended to the synthesis of 3,5-dimethoxy-4-methyl benzoic acid.</p></abstract><textClass xml:lang="en"><keywords scheme="keyword"><list><head>Keywords</head><item><term>alkylation</term></item><item><term>carboxylic acids</term></item><item><term>metalation</term></item></list></keywords></textClass></profileDesc><revisionDesc><change when="2000-02-07">Modified</change><change when="2000">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/6595B27F5E97E6060193E0D50BD6F4D9542CDDA4/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Elsevier, elements deleted: ce:floats; body; tail"><istex:xmlDeclaration>version="1.0" encoding="utf-8"</istex:xmlDeclaration><istex:docType PUBLIC="-//ES//DTD journal article DTD version 4.5.2//EN//XML" URI="art452.dtd" name="istex:docType"><istex:entity SYSTEM="fx1" NDATA="IMAGE" name="fx1"></istex:entity></istex:docType><istex:document><converted-article version="4.5.2" docsubtype="sco" xml:lang="en"><item-info><jid>TETL</jid><aid>16600</aid><ce:pii>S0040-4039(00)00320-8</ce:pii><ce:doi>10.1016/S0040-4039(00)00320-8</ce:doi><ce:copyright type="full-transfer" year="2000">Elsevier Science Ltd</ce:copyright></item-info><head><ce:title>Selective <ce:italic>para</ce:italic> metalation of unprotected 3-methoxy and 3,5-dimethoxy benzoic acids with <ce:italic>n-</ce:italic>butyl lithium–potassium <ce:italic>tert</ce:italic>-butoxide (LIC–KOR): synthesis of 3,5-dimethoxy-4-methyl benzoic acid</ce:title><ce:author-group><ce:author><ce:given-name>Surajit</ce:given-name><ce:surname>Sinha</ce:surname></ce:author><ce:author><ce:given-name>Bhubaneswar</ce:given-name><ce:surname>Mandal</ce:surname></ce:author><ce:author><ce:given-name>Srinivasan</ce:given-name><ce:surname>Chandrasekaran</ce:surname><ce:cross-ref refid="CORR1">*</ce:cross-ref></ce:author><ce:affiliation><ce:textfn>Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India</ce:textfn></ce:affiliation><ce:correspondence id="CORR1"><ce:label>*</ce:label><ce:text>Corresponding author</ce:text></ce:correspondence></ce:author-group><ce:date-received day="6" month="12" year="1999"></ce:date-received><ce:date-revised day="7" month="2" year="2000"></ce:date-revised><ce:date-accepted day="21" month="2" year="2000"></ce:date-accepted><ce:abstract><ce:section-title>Abstract</ce:section-title><ce:abstract-sec><ce:simple-para>The potassium salt of 3-methoxy and 3,5-dimethoxy benzoic acids undergoes deprotonation at the position <ce:italic>para</ce:italic> to the carboxylate group selectively when treated with LIC–KOR in THF at −78°C and it has been extended to the synthesis of 3,5-dimethoxy-4-methyl benzoic acid.</ce:simple-para></ce:abstract-sec></ce:abstract><ce:keywords class="keyword"><ce:section-title>Keywords</ce:section-title><ce:keyword><ce:text>alkylation</ce:text></ce:keyword><ce:keyword><ce:text>carboxylic acids</ce:text></ce:keyword><ce:keyword><ce:text>metalation</ce:text></ce:keyword></ce:keywords></head></converted-article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Selective para metalation of unprotected 3-methoxy and 3,5-dimethoxy benzoic acids with n- butyl lithium–potassium tert -butoxide (LIC–KOR): synthesis of 3,5-dimethoxy-4-methyl benzoic acid</title></titleInfo><titleInfo type="alternative" lang="en" contentType="CDATA"><title>Selective</title></titleInfo><name type="personal"><namePart type="given">Surajit</namePart><namePart type="family">Sinha</namePart><affiliation>Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Bhubaneswar</namePart><namePart type="family">Mandal</namePart><affiliation>Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Srinivasan</namePart><namePart type="family">Chandrasekaran</namePart><affiliation>Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India</affiliation><description>Corresponding author</description><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="brief-communication" displayLabel="Short communication" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-S9SX2MFS-0">brief-communication</genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">2000</dateIssued><dateModified encoding="w3cdtf">2000-02-07</dateModified><copyrightDate encoding="w3cdtf">2000</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><abstract lang="en">Abstract: The potassium salt of 3-methoxy and 3,5-dimethoxy benzoic acids undergoes deprotonation at the position para to the carboxylate group selectively when treated with LIC–KOR in THF at −78°C and it has been extended to the synthesis of 3,5-dimethoxy-4-methyl benzoic acid.</abstract><note type="content">Table 1: </note><subject lang="en"><genre>Keywords</genre><topic>alkylation</topic><topic>carboxylic acids</topic><topic>metalation</topic></subject><relatedItem type="host"><titleInfo><title>Tetrahedron Letters</title></titleInfo><titleInfo type="abbreviated"><title>TETL</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">20000422</dateIssued></originInfo><identifier type="ISSN">0040-4039</identifier><identifier type="PII">S0040-4039(00)X0254-7</identifier><part><date>20000422</date><detail type="volume"><number>41</number><caption>vol.</caption></detail><detail type="issue"><number>17</number><caption>no.</caption></detail><extent 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