I this study, a new series of 1-substituted-3-substitutedpropane-1, 3-diones i.e. β-diketones 4(a-e) have been synthesized from 4-Hydroxy-3-methoxybenzaldehyde i.e. Vanillin which is a phenol as well as aldehyde. The structures of newly synthesized compounds of the series have been established on the basis of usual chemical characteristics, elemental analysis and spectral studies of IR and NMR. They have also been studied for their antimicrobial effects against growth response of bacterial and fungal strains through agar diffusion method.