Journal of Organic Chemistry p. 4658 - 4661 (1983)
Update date:2022-08-04
Topics:
Castaldi, Graziano
Belli, Aldo
Uggeri, Fulvio
Giordano, Claudio
A new method for the synthesis of α-arylalkanoic acids is given, based on Lewis acid promoted rearrangement of acetals of primary and secondary α-haloalkyl aryl ketones (halo = Br, Cl) in hydrocarbon solvents.The reaction is selective, providing the esters of α-arylalkanoic acids in almost quantitative yields.The ability of "soft and borderline" Lewis acids in activating the carbon-halogen bond is compared with that of silver salts.The reaction mechanism is discussed.The present synthesis has been applied to some α-arylpropionic acids well-known as antiinflammatory drugs.
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(1983)
