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Also known as: FC Acylation
Discovered by Charles Friedel, James Crafts (1877)
Lewis acid-catalyzed introduction of an acyl group (C=O-R) onto an aromatic ring. Superior to FC alkylation because: (1) no rearrangements (acylium ion is resonance-stabilized), (2) no polyacylation (product is deactivated), (3) can reduce C=O later for net alkylation.
AlCl₃ reacts with the acyl chloride to form the acylium ion (RC≡O⁺), stabilized by resonance.
No rearrangement — acylium is resonance-stabilized
The acylium ion attacks the aromatic ring, forming the arenium ion.
Deprotonation restores aromaticity. The ketone product coordinates with AlCl₃.
Need > 1 equiv AlCl₃ (product complexes with one equiv)
Benzene + CH₃COCl
AlCl₃ (1.1 equiv)
Acetophenone
Anisole + Succinic anhydride
AlCl₃
4-(4-Methoxyphenyl)-4-oxobutanoic acid
Preferred over FC alkylation for making alkylbenzenes (acylation + reduction). Also gives aryl ketones directly for pharmaceutical synthesis.