Synthesis of Phenylacetic Acids with 2-Oxoalkyl Substituents in the ortho-Position from o-Phenylenediacetic Acid
24 July 2008 (eFirst)
A one-step procedure for the synthesis of 2-(2-oxoalkyl)-substituted phenylacetic acids is described. Very slow addition of organolithium compounds to o-phenylenediacetic acid is the crucial feature to obtain the desired ε-oxo acids in good yields. The selective formation of the ε-oxo acids from the diacid is explained on the basis of hemiketal anion formation.
organometallic reagents - polyanions - carboxylic acids - ketones - nucleophilic addition - heterocycles - ε-oxo acids - hemiketal anions