Nucleophilic Addition Reaction of Aromatic Compounds in the Presence of Lewis Acid

The epoxide 1 obtained by the Darzens condensation reaction of aldehydes with methyl dichloroacetate, reacted with aromatic compounds in the presence of aluminium chloride to afford alpha-aryl- -chloro-alpha-hydroxyalkanoate 3. Scope and limitation of this reaction were studied for various aldehydes and aromatic compounds. The reaction was also studied in the presence of aluminium chloride supported on alumina or silica gel, which is thought to be a mild Lewis acid and harmless for the environment.