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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Phenolate</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><p><b>Phenolate</b> sind in der Chemie Salze der <a href="Phenole" title="Phenole">Phenole</a>. Sie bilden sich aus Phenolen durch die Substitution des H-Atoms der <a href="Hydroxygruppe" title="Hydroxygruppe">Hydroxygruppe</a> durch Metalle.
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<div class="mw-heading mw-heading2"><h2 id="Herstellung">Herstellung</h2></div>
<p>Alkalisalze der Phenole bilden sich durch die Behandlung von Phenolen mit Alkalihydroxid-Lösungen.<sup id="cite_ref-„Lexikon“_1-0" class="reference"><a href="#cite_note-„Lexikon“-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> So bildet sich z. B. <a href="Natriumphenolat" title="Natriumphenolat">Natriumphenolat</a> durch die Einwirkung von <a href="Natronlauge" title="Natronlauge">Natronlauge</a> auf <a href="Phenol" title="Phenol">Phenol</a>.
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<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>Alkaliphenolate – wie Natriumphenolat – sind in wässriger Lösung sehr stark hydrolytisch gespalten, reagieren also basisch.<sup id="cite_ref-„Lexikon“_1-1" class="reference"><a href="#cite_note-„Lexikon“-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Mineralsäuren, Carbonsäuren oder Kohlendioxid setzen aus Phenolat-Lösungen das betreffende Phenol frei. Phenolat-Anionen reagieren als starke Nukleophile und können sowohl an Sauerstoff- wie auch Kohlenstoff-Positionen angegriffen werden.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Generell ist unter kinetisch kontrollierten Bedingungen Angriff am Sauerstoffatom bevorzugt, wohingegen Kohlenstoff-Angriff vor allem unter thermodynamischer Kontrolle beobachtet wird.
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<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>Alkylarylether können beispielsweise durch die <a href="Williamson-Ethersynthese" title="Williamson-Ethersynthese">Williamson-Ethersynthese</a> hergestellt werden. Hierzu wird z. B. <a href="Natriumphenolat" title="Natriumphenolat">Natriumphenolat</a> mit <a href="Halogenalkane" class="mw-redirect" title="Halogenalkane">Alkylhalogeniden</a>, vorzugsweise <a href="Iodide" title="Iodide">Iodiden</a>, zur Reaktion gebracht:<sup id="cite_ref-Beyer_3-0" class="reference"><a href="#cite_note-Beyer-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
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<dl><dd><span class="mwe-math-element mwe-math-element-inline"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle \mathrm {C_{6}H_{5}{-}ONa\ +\ CH_{3}{-}I\longrightarrow \ C_{6}H_{5}{-}O{-}CH_{3}\ +\ NaI} }">
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<annotation encoding="application/x-tex">{\displaystyle \mathrm {C_{6}H_{5}{-}ONa\ +\ CH_{3}{-}I\longrightarrow \ C_{6}H_{5}{-}O{-}CH_{3}\ +\ NaI} }</annotation>
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</math></span><img src="./_assets_/eb734a37dd21ce173a46342d1cc64c92/c8256af5003d0cc470d7fd5470fa2603359c6427.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.671ex; width:52.029ex; height:2.509ex;" alt="{\displaystyle \mathrm {C_{6}H_{5}{-}ONa\ +\ CH_{3}{-}I\longrightarrow \ C_{6}H_{5}{-}O{-}CH_{3}\ +\ NaI} }" loading="lazy"></span></dd>
<dd><small>Reaktion zwischen Natriumphenolat und <a href="Methyliodid" class="mw-redirect" title="Methyliodid">Methyliodid</a> zu Anisol und <a href="Natriumiodid" title="Natriumiodid">Natriumiodid</a></small></dd></dl>
<p>Im großtechnischen Maßstab können anstelle der Alkylhalogenide auch Dialkyl<a href="Sulfate" title="Sulfate">sulfate</a> (beispielsweise <a href="Diethylsulfat" title="Diethylsulfat">Diethylsulfat</a> zur Einführung von <a href="Ethyl" class="mw-redirect" title="Ethyl">Ethylresten</a>) eingesetzt werden:
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<dl><dd><span class="mwe-math-element mwe-math-element-inline"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle \mathrm {C_{6}H_{5}{-}ONa\ +\ (H_{3}CO)_{2}{-}SO_{2}\longrightarrow \ C_{6}H_{5}{-}O{-}CH_{3}\ +\ (H_{3}CO)SO_{3}Na} }">
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<annotation encoding="application/x-tex">{\displaystyle \mathrm {C_{6}H_{5}{-}ONa\ +\ (H_{3}CO)_{2}{-}SO_{2}\longrightarrow \ C_{6}H_{5}{-}O{-}CH_{3}\ +\ (H_{3}CO)SO_{3}Na} }</annotation>
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</math></span><img src="./_assets_/eb734a37dd21ce173a46342d1cc64c92/d8ea9e1c5400f0494fbeadd75288803fbfe33379.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.838ex; width:71.424ex; height:2.843ex;" alt="{\displaystyle \mathrm {C_{6}H_{5}{-}ONa\ +\ (H_{3}CO)_{2}{-}SO_{2}\longrightarrow \ C_{6}H_{5}{-}O{-}CH_{3}\ +\ (H_{3}CO)SO_{3}Na} }" loading="lazy"></span></dd>
<dd><small>Reaktion zwischen Natriumphenolat und <a href="Dimethylsulfat" title="Dimethylsulfat">Dimethylsulfat</a> zu Anisol.</small></dd></dl>
<div class="mw-heading mw-heading3"><h3 id="Technische_Herstellung_von_Salicylsäure"><span id="Technische_Herstellung_von_Salicyls.C3.A4ure"></span>Technische Herstellung von Salicylsäure</h3></div>
<p><a href="Salicyls%C3%A4ure" title="Salicylsäure">Salicylsäure</a> wird durch die <a href="Kolbe-Schmitt-Reaktion" title="Kolbe-Schmitt-Reaktion">Kolbe-Schmitt-Reaktion</a> (vereinfacht auch als Salicylsäure-Synthese bezeichnet) aus <a href="Kohlenstoffdioxid" title="Kohlenstoffdioxid">CO<sub>2</sub></a> und <a href="Natriumphenolat" title="Natriumphenolat">Natriumphenolat</a> hergestellt:
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<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-„Lexikon“-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-„Lexikon“_1-0">a</a></sup> <sup><a href="#cite_ref-„Lexikon“_1-1">b</a></sup></span> <span class="reference-text">Hans-Dieter Jakubke, Ruth Karcher (Koordinatoren): <i>Lexikon der Chemie</i> in drei Bänden, Spektrum Verlag, Heidelberg, Band 3, 1999, ISBN 3-8274-0381-2, S. 14.</span>
</li>
<li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text">Robert J. Mayer, Martin Breugst, Nathalie Hampel, Armin R. Ofial, Herbert Mayr: <cite style="font-style:italic">Ambident Reactivity of Phenolate Anions Revisited: A Quantitative Approach to Phenolate Reactivities</cite>. In: <cite style="font-style:italic">Journal of Organic Chemistry</cite>. 26. Juni 2019, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1021/acs.joc.9b01485">10.1021/acs.joc.9b01485</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:Phenolate&rft.atitle=Ambident+Reactivity+of+Phenolate+Anions+Revisited%3A+A+Quantitative+Approach+to+Phenolate+Reactivities&rft.au=Robert+J.%26%2332%3BMayer%2C%26%2332%3BMartin%26%2332%3BBreugst%2C%26%2332%3BNathalie%26%2332%3BHampel%2C+...&rft.btitle=Journal+of+Organic+Chemistry&rft.date=2019-06-26&rft.doi=10.1021%2Facs.joc.9b01485&rft.genre=book" style="display:none"> </span></span>
</li>
<li id="cite_note-Beyer-3"><span class="mw-cite-backlink"><a href="#cite_ref-Beyer_3-0">↑</a></span> <span class="reference-text"><a href="Hans_Beyer" title="Hans Beyer">Hans Beyer</a> und <a href="Wolfgang_Walter" title="Wolfgang Walter">Wolfgang Walter</a>: <i>Organische Chemie</i>, S. Hirzel Verlag, Stuttgart, 1984, S. 463–464, ISBN 3-7776-0406-2.</span>
</li>
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