Abstract
Friedel–Crafts hydroxyalkylation of 2-methoxynaphthalene, anisole and 2-methylfuran with paraformaldehyde has been carried out in N-ethyl-N′-methylimidazolium chloride (1+Cl-) or N-butyl-N′-methylimidazolium hexafluorophosphate (2+PF- 6) or ethanol using concentrated aqueous HCl as catalyst. The results have shown an extraordinary activity and selectivity towards the formation of the corresponding hydroxymethyl derivative using 2+PF- 6 as solvent. This sharply contrasts with the case of the ethanol as solvent wherein the reaction is much slower and diarylation products are largely formed.
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Formentín, P., García, H. Ionic Liquids as Exceedingly Convenient Solvents for the Friedel–Crafts Monoalkylation of Electron-Rich Arenes with Paraformaldehyde Using HCl as Catalyst. Catalysis Letters 78, 115–118 (2002). https://doi.org/10.1023/A:1014993609650
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DOI: https://doi.org/10.1023/A:1014993609650