A series of novel racemic 2-(1,3-diaryl-3-hydroxypropyl)cyclohexan-1-ol derivatives were synthesized from 1,5-diketones. All the synthesized compounds were characterized by spectroscopic methods. The antibacterial activities of obtained chiral 1,5-diols were investigated against four Gram-positive and three Gram-negative bacteria by determining of minimum inhibitory concentrations (MICs) in vitro. Compounds 3b, 3c, and 3d were found to be active against Enterococcus faecalis and Escherichia coli. In addition, compound 3j were found to be moderately active against all tested bacterial strains.