NATURAL PRODUCT RESEARCH AND DEVELOPMENT ›› 2017, Vol. 29 ›› Issue (9): 1573-1579. doi: 10.16333/j.1001-6880.2017.9.021

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Alkali-catalyzed Synthesis of 4-Methyl-2′-hydroxyl-4′-methoxychalcone and Its Crystal Structure

LIU Cun-fang*, WANG Jun-hong, SHAO Xian-zhao, WU Rui   

  1. Shaanxi Key Laboratory for Catalysis, Shaanxi University of Technology, Hanzhong 723000, China
  • Online:2017-09-27 Published:2017-09-27

Abstract: The synthesis method of chalcone was investigated under the assistance of ultrasonic irradiation with alkali as the catalyst.A novel paeonol derivative named 4-methyl-2′-hydroxyl-4′-methoxychalcone was synthesized in alkaline medium under the assistance of ultrasonic irradiation,the reaction of paeonol and 4-methylbenzaldehyde was by Claisen-Schmidt condensation reaction at room temperature,its yield reached 71.57%,its structure existing 1,3-diphenyl acrylic ketone was characterized by UV,IR,MS,1H NMR, 13C NMR and 135° DEPT.The crystal structure of 4-methyl-2′-hydroxyl-4′-methoxychalcone was also characterized by Xray structure analysis,its crystal belonged to space group P2(1)/n in triclinic crystallographic system,and its cell parameters: a=1.1288(10) nm, b=0.6916(6)nm, c=2.0509(4) nm, α=90.0(8)°, β =109.8(8)°, γ=90(8) °,V=1.4056 (5) nm3, Dc=1.272 mg/cm3.The novel paeonol derivative existing 1,3-diphenyl acrylic ketone in the molecular structure was synthesized through the reaction of paeonol and 4-methylbenzaldehyde under the assistance of ultrasonic irradiation with alkali as the catalyst.

Key words: paeonol, synthesis, Claisen-Schmidt condensation reaction, chalcone, crystal structure

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