Perkin reaction

<h2 id="reaction--mechanism">Reaction  mechanism</h2>

<p>Clear from the reaction mechanism, the anhydride of aliphatic acid must contain at least 2 α-H for the reaction to occur. The above mechanism is not universally accepted, as several other versions exist, including decarboxylation without acetic group transfer.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a>
</p>
<h2 id="applications">Applications</h2>
<ul><li>Salicylaldehyde converted to <a href="/facts/Coumarin/bW8bsSzK">coumarin</a> using acetic anhydride with acetate as base.<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a></li>
<li>cinnamic acid is prepared from <a href="/facts/Benzaldehyde/GyboW1KC">benzaldehyde</a>, again using acetic anhydride in the presence of sodium or potassium acetate.</li>
<li><a href="/facts/Resveratrol/5sF3fvl7">resveratrol</a> (c.f. <a href="/facts/Fo-ti/7qUKNjhm">fo-ti</a>), a <a href="/facts/Phytoestrogens/lsLPIK1k">phytoestrogenic</a> <a href="/facts/Stilbene/RT7dCGhr">stilbene</a> is yet another product of this methodology.<a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a></li></ul>
<h2 id="see-also">See also</h2>
<ul><li><a href="/facts/Erlenmeyer%E2%80%93Pl%C3%B6chl_azlactone_and_amino-acid_synthesis/LlQvn0sv">Erlenmeyer–Plöchl azlactone and amino-acid synthesis</a></li>
<li><a href="/facts/Stobbe_condensation/XDXF7TMJ">Stobbe condensation</a></li>
<li><a href="/facts/Pechmann_condensation/NBAGXd8n">Pechmann condensation</a></li></ul>

<h2 id="references">References</h2>

<ol>
<li id="fn:1"><p>Perkin, W. H. (1868). "On the artificial production of coumarin and formation of its homologues". Journal of the Chemical Society. 21: 53–61. doi:10.1039/js8682100053. <a href="https://babel.hathitrust.org/cgi/pt?id=mdp.39015077817479;view=1up;seq=65" target="_blank">https://babel.hathitrust.org/cgi/pt?id=mdp.39015077817479;view=1up;seq=65</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li>
<li id="fn:2"><p>Perkin, W. H. (1877). "On some hydrocarbons obtained from the homologues of cinnamic acid; and on anethol and its homologues". Journal of the Chemical Society. 32: 660–674. doi:10.1039/js8773200660. <a href="https://babel.hathitrust.org/cgi/pt?id=mdp.39015077817446;view=1up;seq=1444" target="_blank">https://babel.hathitrust.org/cgi/pt?id=mdp.39015077817446;view=1up;seq=1444</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li>
<li id="fn:3"><p>Dippy, J. F. J.; Evans, R. M. (1950). "The nature of the catalyst in the Perkin condensation". J. Org. Chem. 15 (3): 451–456. doi:10.1021/jo01149a001. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li>
<li id="fn:4"><p>Johnson, J. R. (1942). "The Perkin Reaction and Related Reactions". Org. React. 1: 210–265. doi:10.1002/0471264180.or001.08. ISBN 0471264180. {{cite journal}}: ISBN / Date incompatibility (help) <a href="0471264180" target="_blank">0471264180</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li>
<li id="fn:5"><p>House, H. O. (1972) Modern Synthetic Reactions, W. A. Benjamin, Menlo Park, California, 2nd ed, pp. 660–663 <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li>
<li id="fn:6"><p>Rosen, T. (1991). "The Perkin Reaction". Compr. Org. Synth. 2: 395–408. doi:10.1016/B978-0-08-052349-1.00034-2. ISBN 978-0-08-052349-1. <a href="978-0-08-052349-1" target="_blank">978-0-08-052349-1</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li>
<li id="fn:7"><p>Bansal, Raj K. (1998) Organic Reaction Mechanisms, Tata McGraw Hill, 3rd Edition , pp. 199–201, ISBN 9780470858585 doi:10.1002/0470858583. <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li>
<li id="fn:8"><p>Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–45. doi:10.1002/14356007.t11_t02. ISBN 978-3-527-30673-2. <a href="978-3-527-30673-2" target="_blank">978-3-527-30673-2</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li>
<li id="fn:9"><p>Solladié, Guy; Pasturel-Jacopé, Yacine; Maignan, Jean (2003). "A re-investigation of resveratrol synthesis by Perkins reaction. Application to the synthesis of aryl cinnamic acids". Tetrahedron. 59 (18): 3315–3321. doi:10.1016/S0040-4020(03)00405-8. ISSN 0040-4020. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li>
</ol>

Perkin reaction open-in-new

Perkin reaction