Gattermann reaction

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 aluminium chloride (AlCl3). It is named for the German chemist Ludwig Gattermann and is similar to the Friedel–Crafts reaction.

For the conversion of benzenediazonium chloride to a haloarene (also referred to as the 'Gattermann reaction'), see Diazonium compound § Gattermann reaction.
Gattermann formylation
Named after Ludwig Gattermann
Reaction type Substitution reaction
Identifiers
RSC ontology ID RXNO:0000139

Modifications have shown that it is possible to use sodium cyanide or cyanogen bromide in place of hydrogen cyanide.

The reaction can be simplified by replacing the HCN/AlCl3 combination with zinc cyanide. Although it is also highly toxic, Zn(CN)2 is a solid, making it safer to work with than gaseous HCN. The Zn(CN)2 reacts with the HCl to form the key HCN reactant and Zn(Cl)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.

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