80336-89-6Relevant articles and documents
A Lewis Acid Catalyzed 1,2 Aryl Shift in α-Haloalkyl Aryl Acetals: A Convenient Route to α-Arylalkanoic Acids
Castaldi, Graziano,Belli, Aldo,Uggeri, Fulvio,Giordano, Claudio
, p. 4658 - 4661 (2007/10/02)
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.