Aldol Condensation of Diacetybenzene with Benzaldehyde Containing a Hydroxyl Group Catalyzed by p-Toluenesulfonic Acid

Using p-toluenesulfonic acid (p-TsOH) as a catalyst, three 1,3-bis[3-(substituted phenyl) acryloyl]benzene derivatives 1 similar to 3, three 1,4-bis[3-(substituted phenyl)acryloyl]benzene derivatives 4 similar to 6 and two intermediate compounds 7, 8 were synthesized by cross aldol condensations of diacetybenzene with benzaldehyde containing a hydroxyl group. Three 1-[3-(4-hydroxy-phenyl)acryloyl]-4-[3-(substituted phenyl)acryloyl] benzene derivatives 9 similar to 11 were obtained by aldol condensations of intermediate compounds 7, 8 with benzaldehyde containing a hydroxyl group. The method was very convenient, and the reaction time was for 2 similar to 6 d. The structures of all new compounds were characterized by H-1 NMR, IR, and HRMS techniques