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2.5.7.3 Formylation with Carbon Monoxide

DOI: 10.1055/sos-SD-213-00191

Zhang, N.; Dong, D.Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (20142335.

Similar to the Friedel–Crafts acylation reaction, the Gattermann–Koch reaction, in which carbon monoxide and hydrochloric acid are used with a Friedel–Crafts catalyst (i.e., AlCl3), can efficiently convert benzene derivatives into the corresponding benzaldehydes.[‌7‌‌10‌] Benzaldehyde and many other aromatic aldehydes 6 are conveniently synthesized by this reaction (Scheme 3). The alkyl group in monoalkylbenzenes directs the aldehyde group almost exclusively to the para position. The key variables in the Gattermann–Koch reaction are the amount of catalyst, the concentration of the reagent in the solvent, the pressure, and the temperature. The presence of a trace amount of copper(I) chloride is also needed.

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