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25.6.6.11 Method 11: The Gattermann–Koch Reaction

DOI: 10.1055/sos-SD-025-00443

Schall, A.; Reiser, O.Science of Synthesis, (200725642.

Formyl chloride, which is only stable at the temperature of liquid air, can be generated in situ by reacting dry hydrogen chloride and carbon monoxide in the presence of aluminum trichloride and copper(I) chloride. This way, the GattermannKoch reaction can proceed readily at an ambient pressure of carbon monoxide, while in the absence of copper(I) chloride, pressures of 1020MPa of carbon monoxide have to be employed. It is speculated that the reaction is promoted by the formation of both a copper(I) chloridecarbon monoxide adduct and an aluminum trichloride complex [HCO(AlCl4)]. Nevertheless, the variable yields often obtained with this process limit its applicability. Alkylated arenes 41 can be employed as substrates (Scheme 23) to give the corresponding aromatic aldehydes 42, while strongly electron-withdrawing substituents (e.g., hydroxy and alkoxy groups) are not tolerated.[‌3‌,‌133‌]

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