Objective: To synthesize 4,2′-dihydroxy chalcone and its analogs.Method:4,2′-dihydroxy chalcone and 5 analogs were synthesized via aldol condensation with 4-hydroxy benzaldehydes and 2-hydroxy acetophenones as reactants and piperidine as catalyst.Results: 4,2′-dihydroxy chalcone and 5 analogs were successfully obtained at satisfying yields and structurally confirmed via MS、1H-NMR、and IR.Conclusion:Piperidine shows satisfying effects and deserves further research as a promising catalyst in aldol condensation.