Hoesch reaction
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 hydrochloric acid and a Lewis acid catalyst.
An example is the synthesis of 1-(2,4,6-trihydroxyphenyl)ethanone from phloroglucinol:[1]
A ketimine is 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.
References
- ^ Organic Syntheses, Coll. Vol. 2, p.522 (1943); Vol. 15, p.70 (1935). http://www.orgsynth.org/orgsyn/pdfs/CV2P0522.pdf
- ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition, New York: Wiley, 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