Alkylation reaction and Michael condensation of 3 aroyl acrylic acids

ABSTRACT

It is reported that when Beta [3,4-dichloro]-benzoyl acrylic acid was treated with aromatic hydrocarbons and aluminum chloride, addition occurred alpha to carboxyl group. In this study this method has been applied to Beta [p-phenyl]-benzoyl acrylic acid la, to augment the reactivity of the aroyl acrylic acids to react as alpha, Beta-unsaturated ketones rather than alpha, Beta-unsaturated acids in which the polar factor increases. The acid la undergoes addition reaction with p-xylene under Friedel Crafts conditions to give the corresponding alpha-[2, 5-dimethyl]-phenyl-Beta-[p-phenyl]-benzoyl propionic acid [II]. The structure of the resultant acid II was derived from its spectral data. IR spectrum showed bands due to ketonic C=O [1680], carboxylic CO [1710] and OH [3300-3000]. The PMR spectrum [CDC1[3]] showed signals at 229 and 236 [6H, s, of Ar-CH[3]], 2.80-3-50 [dxd, 2H of non equivalent CH[2]], 3-95-4-3 [m, IH of >CH-] and 7-7-8 [m, 12H of Ar-H]