A series of new phthalides of pharmacological interest were synthesized by a protocol involving condensation of two c-keto acids, 2-(4-isopropylbenzoyl)benzoic acid (1a) and 2-(4-isopropyl-3-nitrobenzoyl)benzoic acid (1b) with phenolic compounds in the presence of catalytic quantity of concentrated sulphuric acid. The method is simple, efficient, economical and environmentally benign as the reaction is carried out under solvent free condition attempting a green approach. Structural characterization of these newly synthesized compounds was accomplished by IR, UV, 1 H NMR, 13C NMR, Mass spectral data, elemental analysis and chemical reactions. Some of the synthesized phthalides were found to exhibit antifungal and antibacterial activity against various human pathogenic bacterial and fungal strains.