Friedel-Crafts

Alkylation or acylation of aromatic compounds with alkyl or acyl halides in the presence of aluminum chloride.

 

Condensed polycyclic hydrocarbons and some heterocyclic compounds can react by a similar pathway.

Veismeier-Haak modification - acylation of aromatic compounds with anilides.

Nencki modification - a) acylation of phenols with carboxylic acids in the presence of zinc(II) chloride; b) utilizes iron(III) chloride instead od aluminum chloride.

Behn modification - with nitrobenzene as solvent.

Perrier modification - preparation of aluminum chloride complex with RCOX to increase the yield.

Friedel-Crafts-Perrier method - synthesis of nitriles from aromatic compounds and freshly prepared halocyanides.

Also see Anschütz, Balsohn, Nenitzescu and Radziewanowski.

Bibliography

• Friedel C. Crafts J. M., C. R., 1877, 84, 1392, 1450.
• Gourmelen C., Gaff Y., Le Tutour B., Bull. Soc. Chim. France, 1974, No.7-8, 2, 1715.
• OR, 2, 141; 3, 7; 5, 195.
• Olah G. A., Friedel-Crafts and Related Reactions, I-IV, New York-London, Interscience, 1963-1965.