The Hoesch reaction or Houben–Hoesch reaction is an organic reaction in which a nitrile reacts with an arene compound to form an aryl ketone. The reaction is a type of Friedel-Crafts acylation with hydrogen chloride and a Lewis acid catalyst.
The synthesis of 2,4,6-Trihydroxyacetophenone (THAP) from phloroglucinol is representative:[1] If two-equivalents are added, 2,4-Diacetylphloroglucinol is the product.
Hoesch reaction example, 1-(2,4,6-trihydroxyphenyl)ethanone from phloroglucinol
An imine can be isolated as an intermediate reaction product. The attacking electrophile is possibly[2] 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 Gattermann reaction in which hydrocyanic acid not a nitrile is used.
The reaction is named after Kurt Hoesch[3] and Josef Houben[4] who reported about this new reaction type in respectively 1915 and 1926.
^Gulati, K. C.; Seth, S. R.; Venkataraman, K. (1935). "Phloroacetophenone". Organic Syntheses. 15: 70. doi:10.15227/orgsyn.015.0070.
^March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition, New York: Wiley, p. 732, ISBN 9780471854722, OCLC 642506595
^Eine neue Synthese aromatischer Ketone. I. Darstellung einiger Phenol-ketone Berichte der deutschen chemischen Gesellschaft Volume 48, Issue 1, Date: Januar–Juni 1915, Pages: 1122–1133 Kurt Hoesch doi:10.1002/cber.191504801156
^Über die Kern-Kondensation von Phenolen und Phenol-äthern mit Nitrilen zu Phenol- und Phenol-äther-Ketimiden und -Ketonen (I.) Berichte der deutschen chemischen Gesellschaft (A and B Series) Volume 59, Issue 11, Date: 8. Dezember 1926, Pages: 2878–2891 J. Houben doi:10.1002/cber.19260591135
The Hoeschreaction or Houben–Hoeschreaction is an organic reaction in which a nitrile reacts with an arene compound to form an aryl ketone. The reaction...
can be prepared in the Friedel–Crafts acylation, the related Houben–Hoeschreaction, and the Fries rearrangement. Ozonolysis, and related dihydroxylation/oxidative...
participate in the reaction and hence would be expected to react more readily under basic rather than acidic conditions. Hoeschreaction Overman rearrangement...
By reaction of alkenes with hydrazoic acid in the Schmidt reaction. By reaction of a nitrile, hydrochloric acid, and an arene in the Hoeschreaction. Multicomponent...
creatine Nitriles react in Friedel–Crafts acylation in the Houben–Hoeschreaction to ketones In reductive decyanation the nitrile group is replaced by...
at 218–220 °C. It does not boil intact, but it does sublime. The Hoeschreaction allows the synthesis of 1-(2,4,6-Trihydroxyphenyl)ethanone from phloroglucinol...
also obtained from reaction with nitriles, by the Houben–Hoeschreaction. Pyrrole aldehydes can be formed by a Vilsmeier–Haack reaction. The NH proton in...
the preparation of the drug flopropione by the Houben-Hoeschreaction. The nitrile aldol reaction with benzophenone, followed by reduction of the nitrile...
acts as a COMT inhibitor. It is synthesized from phloroglucinol in a Hoeschreaction. 2,4,6-Trihydroxyacetophenone (THAP) Buckingham J, MacDonald F (26...
head of the war laboratory. He improved the Hoeschreaction which is now normally called Houben-Hoeschreaction. Houben organized and made a major rework...
transient intermediates in certain metal-catalyzed reactions of nitriles, such as the Hoeschreaction and the hydrogenation of nitriles. In some cases,...
converted into the chlorine compounds. In a Hoeschreaction, aromatic hydroxyketones are formed in the reaction of substituted phenols with trichloroacetonitrile...
benzophenone intermediate. The Robinson-Nishikawa method is a variant of the Hoesch synthesis but with low yields. The Asahina-Tanase method synthesizes some...
hydrochloric acid to give Bufomedil (3). This is a demonstration of the Hoeschreaction. "Buflomedil-Containing Drugs May Be Suspended in EU". Medscape. Retrieved...
Species as the Reactive Intermediates in Gattermann, Houben-Hoesch, and Friedel-Crafts Reactions of Nonactivated Benzenes". Journal of the American Chemical...
the process was introduced at a smelter in Neuwied, followed by Eberhard Hoesch's Lendersdorf smelter near Düren in 1825, and Harkort's plant a year later...
procedures. Such procedures include Gattermann aldehyde synthesis, Houben-Hoesch ketone synthesis, and the Beckmann rearrangement. Their chemistry is related...
afforded by tariffs and to cartels. The leading firm was "Friedrich Krupp AG Hoesch-Krupp" run by the Krupp family. The "German Steel Federation" was established...
Ambassador to Ireland (1937–1945) Walther Hewel: German diplomat Leopold von Hoesch: German Ambassador to France (1923–1932) and the United Kingdom (1932–1936)...
afforded by tariffs and cartels. The leading firm was "Friedrich Krupp AG Hoesch-Krupp", run by the Krupp family. The merger of several major firms into...
Wang ZJ, Zhang Y, Weng HM, Prabhakaran D, Mo S-K, Peng H, Dudin P, Kim T, Hoesch M, Fang Z, Dai X, Shen ZX, Feng DL, Hussain Z & Chen YL 2014, 'A Stable...
Agostini Rizzoli Arte et Cultura. ISBN 8873170951. Eimert, Dorothea; Leopold-Hoesch-Museum der Stadt Düren, eds. (1986-01-01). 1. Internationale Biennale der...
War Secretary Alfred Duff Cooper told the German Ambassador Leopold von Hoesch on 8 March: "though the British people were prepared to fight for France...
Die Neuen Tendenzen, Museum fűr kronkrete Kunst, Ingolstadt 2007 Leopold-Hoesch-Museum, Dűren; Op Art, Schirn Kunsthalle, Frankfurt; Optic Nerve. Perceptual...
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