0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via 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]

Meeeee 88 MeeeeeeeeeMeee Meeeeeeeeee[‌888‌‌888‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee (%) Mee
M M M 88 [‌888‌]
M Me M 88 [‌888‌]
M Me M 88 [‌888‌]
M Me M 88 [‌888‌]
Me Me Me 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeeee (88, M8=M8=M; M8=Me); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

MMMMMMM: Meeeeeee eeeeeeeeeee eeee ee e eeeeee eeeeeeee ee eee eeeeeee eee eeeeee eeeeeeeee eeee eeeee.

M eeeeee ee eee MM eee MMe eee eeeeee eee 8e eeee e eeee-eeeeeee eeee ee eeeeeeee (88e, 8.88eee) ee eee eeeeeee (888eM) (MMMMMMM: eeeeeeeeee) eeeeeeeeee eeeee MeMe8 (88e, 8.88eee) eee MeMe (88e, 8.88eee) ee 8888°M. Meeee eeeeeeee eeeeeeeee, eee eeee eeeeeee, eeeeeeeee eeeeeee eee eeeeee eeee eee, eeee eeeee e eeeeee eee eeeeeeeee. Mee eeeeeee eee eeeee eeeeeeeee ee eeeeee eeeeeee eee eeeeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee eeee Me8M, eee eeeeeee eee eeeeee eeee eee MMe eee eeee M8M, eee eee Me8M eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeee eeeeeee eeeeeeee eee eeeeee eeee ee eeeeee ee eee. MeMMM8, eee eeeee 88e, eee eeeee eeeeeeeee eeeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee MeMM eee Me8M, eee eeeeee eeee ee Me8MM8. Mee eeeeeeee eee eeee eeeeeeeee, eeeee ee e eeeeee eeeee, eee eeeeeeeeeeeeee [eeeeeeeee eeeee (ee 88888°M), 8×] ee eeee eeee eeeeee eeeeee ee eee eeeee eeeeeeee; eeeee: 88e (88%); ee 88°M.