An efficient procedure for the synthesis of polyhydroxyl aromatic compounds (phloroglucide analogs) is described. In this procedure a reaction was done between different 4-substituted phenols and 2,6-bis(hydroxymethy) phenols. The reactions proceed in the presence of catalytic amount of silica gel supported boric tri-sulfuric anhydride (SiO2-BTSA) in excellent yields. 16 compounds were synthesized (I1-I16). Chemical structures of all compounds were confirmed by spectroscopic methods. We optimized the chemical reactions in the presence of different acidic catalysts, different solvents and also different temperatures. Catalytic amounts of SiO2-BTSA in dichloroethane (DCE) was the best conditions. Some of the synthesized compounds were screened for their antimicrobial activities. Antifungal and antibacterial activities of the synthesized compounds were evaluated by broth micro dilution method as recommended by CLSI. Some of the tested compounds show good in vitro biological properties.