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Hoesch reaction
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<p>The Hoesch reaction or Houben–Hoesch reaction is an <a href="/facts/Organic_reaction/SESmeGWm">organic reaction</a> in which a <a href="/facts/Nitrile/Gz7RCnC6">nitrile</a> reacts with an <a href="/facts/Arene_compound/3EXq8Tgf">arene compound</a> to form an aryl <a href="/facts/Ketone/BqQXpLo4">ketone</a>. The reaction is a type of <a href="/facts/Friedel%25E2%2580%2593Crafts_acylation/N65aEdXA">Friedel–Crafts acylation</a> with <a href="/facts/Hydrogen_chloride/7Wzkhomd">hydrogen chloride</a> and a <a href="/facts/Lewis_acid/qlLqRvg2">Lewis acid</a> <a href="/facts/Catalyst/LPBS7TQC">catalyst</a>. </p><p>The synthesis of <a href="/facts/2%2c4%2c6-Trihydroxyacetophenone/5KRfeNRb">2,4,6-Trihydroxyacetophenone</a> (THAP) from <a href="/facts/Phloroglucinol/jkQwf8Hw">phloroglucinol</a> is representative: If two-equivalents are added, <a href="/facts/2%2c4-Diacetylphloroglucinol/W0ymRGbc">2,4-Diacetylphloroglucinol</a> is the product. </p> <p>An <a href="/facts/Imine/yK72z07j">imine</a> can be isolated as an intermediate reaction product. The attacking <a href="/facts/Electrophile/1AHFg1zm">electrophile</a> is possibly a species of the type R-C+=NHCl−. The arene must be electron-rich i.e. phenol or aniline type. A related reaction is the <a href="/facts/Gattermann_reaction/sNvenw3z">Gattermann reaction</a> in which hydrocyanic acid not a nitrile is used. </p><p>The reaction is named after Kurt Hoesch and <a href="/facts/Josef_Houben/BXknkhpL">Josef Houben</a> who reported about this new reaction type in respectively 1915 and 1926. </p>