Abstract This paper reports on the synthesis of 3-(3-hydroxy-4-methoxyphenyl)-1-phenylprop-2-en-1-one by Claisen-Schmidt condensation of acetophenone with an aromatic aldehyde (vanillin) in the presence of aqueous solution of 60% sodium hydroxide at room temperature. The percentage yield of 3-(3-hydroxy-4-methoxyphenyl)-1-phenylprop-2-en-1-one was found to be 32.3% after recrystallization from ethanol. The synthesized 3-(3-hydroxy-4-methoxyphenyl)-1-phenylprop-2-en-1-one was characterized using Fourier Transform Infrared (FTIR) spectroscopy, Shinoda’s test, and melting point measurement. The synthesized compound was tested for its antibacterial activities by cup plate method against the bacterial strains of Staphylococcus Aureus, Pseudomonas Aeruginosa, Bacillus subtilis, and Escherichia coli. Gentamicin was used as the control for the antimicrobial screening. The synthesized of 3-(3-hydroxy-4-methoxyphenyl)-1-phenylprop-2-en-1-one was did not show antimicrobial activity at the doses used.