Gattermann reaction

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Gattermann formylation
Named after Ludwig Gattermann
Reaction type Substitution reaction
Identifiers
RSC ontology ID RXNO:0000139

The Gattermann reaction, (also known as the Gattermann formylation and the Gattermann salicylaldehyde synthesis) is a chemical reaction in which aromatic compounds are formylated by a mixture of hydrogen cyanide (HCN) and hydrogen chloride (HCl) in the presence of a Lewis acid catalyst such as AlCl3. It is named for the German chemist Ludwig Gattermann[1] and is similar to the Friedel–Crafts reaction.

Gattermann I.png
Gattermann II.png

The reaction can be simplified by replacing the HCN/AlCl3 combination with zinc cyanide.[2] Although it is also highly toxic, Zn(CN)2 is a solid, making it safer to work with than gaseous HCN.[3] The Zn(CN)2 reacts with the HCl to form the key HCN reactant and Zn(CN)2 that serves as the Lewis-acid catalyst in-situ. An example of the Zn(CN)2 method is the synthesis of mesitaldehyde from mesitylene.[4]

Gattermann–Koch reaction[edit]

Gattermann–Koch formylation
Named after Ludwig Gattermann
Julius Arnold Koch
Reaction type Substitution reaction

The Gattermann–Koch reaction, named after the German chemists Ludwig Gattermann and Julius Arnold Koch,[5] is a variant of the Gattermann reaction in which carbon monoxide (CO) is used instead of hydrogen cyanide.[6]

Gattermann-Koch.svg

Unlike the Gattermann reaction, this reaction is not applicable to phenol and phenol ether substrates.[3] Additionally, when zinc chloride is used as the catalyst, the presence of traces of copper(I) chloride co-catalyst is often necessary.

See also[edit]

References[edit]

  1. ^ Gattermann, L.; Berchelmann, W. (1898). "Synthese aromatischer Oxyaldehyde". Berichte der deutschen chemischen Gesellschaft. 31 (2): 1765–1769. doi:10.1002/cber.18980310281.
  2. ^ Adams R.; Levine, I. (1923). "Simplification of the Gattermann Synthesis of Hydroxy Aldehydes". J. Am. Chem. Soc. 45 (10): 2373–77. doi:10.1021/ja01663a020.
  3. ^ a b Adams, Roger (1957). Organic Reactions, Volume 9. New York: John Wiley & Sons, Inc. pp. 38 & 53–54. doi:10.1002/0471264180.or009.02. ISBN 9780471007265.
  4. ^ Fuson, R. C.; Horning, E. C.; Rowland, S. P.; Ward, M. L. (1955). "Mesitaldehyde". Organic Syntheses. doi:10.15227/orgsyn.023.0057.; Collective Volume, 3, p. 549
  5. ^ Gattermann, L.; Koch, J. A. (1897). "Eine Synthese aromatischer Aldehyde". Chemische Berichte. 30: 1622. doi:10.1002/cber.18970300288.
  6. ^ Li, Jie Jack (2003). Name Reactions: A Collection of Detailed Reaction Mechanisms (available on Google Books) (2nd ed.). Springer. p. 157. ISBN 3-540-40203-9.