ABSTRACT. Totally twelve title compounds have been synthesized by Claisen-Schmidt condensation of (E)-methyl 2-(2-(((1-acetylnaphthalen-2-yl)oxy)methyl)phenyl)-3-methoxy acrylate and substituted benzaldehydes in presence of catalytic quantity of LiOH.H 2 O catalyst under stirring in room temperature. The yields of the compounds are more than 92%. The synthesized titled compounds were characterized by their physical constants, IR, NMR and Mass spectral data. The spectral data such as infrared ν CO s-cis , s-trans , CO ester , NMR chemical shifts (δ, ppm) of H α , H β , C α , C β , CO of enone moiety, H βʹ and CO of acrylate moieties have been correlated with Hammett substituent constants, F and R parameters. The antimicrobial, antioxidant and insect antifeedant activities of all synthesized compounds have been evaluated using corresponding bacterial and fungal strains, DPPH radical scavenging and Disc diffusion bio-assay of 4 th instar larvae Achoea Janata L with castor-leaf discs.