Study On Claisen-Schmidt Condensation Of 6-Methoxy-2-Naphthaldehyde And Acetone In Ionic Liquids-Assisted Catalyst

The organic compounds containingα,β-unsaturated ketene structure have been studied widely, because of the existing conjugate function between carbonyl group and unsaturated double bond. It means that these organic compounds have good reaction activity, so they are treated as important precursors or reactive intermediates in the process synthesis of drug with ring or chiral carbon center. The medicine synthesized byα,β-unsaturated ketene containing organic compounds, which have special effects as follows: anticancer, antifungal, antioxidant, sedative hypnotics, anti-inflammatory, immuneomodulatory, cardiovascular protection etc.After comparing the characteristic of different catalyst on reaction, the readily available, easily prepared and widely used raw material sodium hydroxide was selected as main catalyst alone with aqueous was studied in this paper. The main study has the following aspects.First of all, catalyst research on synthesis ofα,β-unsaturated ketene was introduced, and detailed review about the status ofα,β-unsaturated ketene in the application of drugs producing was made.Secondly, a series of catalyst were designed based on structural characteristic ofα,β-unsaturated ketene and imidazolium ionic liquid. (1) Claisen-Schmidt condensation between 6-methoxy-2-naphthalene formaldehyde and acetone based on literature was repeat, which was catalyzed by the system composed of sodium, aqueous, ethanol; (2) Impact of the reaction temperature, time and the types of catalyst were studied. The optimized reaction condition was set as follow: the temperature was 35℃, reaction time was 60min, sodium hydroxide mass fraction was 25%, and the target product yield was 56%; (3) Different mole ratio of 6-methoxy-2-naphthalene formaldehyde and acetone on product yield was studied in the article. The optimized mole ratio of reaction was set 1 to 1.5; (4) Different effect of three water-soluble imidazolium ring containing ionic liquids [Bmim]Cl, [Bmim]BF4, [Bmim]PF6 on Claisen-Schmidt condensation of 6- methoxy-2-naphthalene and acetone were studied, the organic solutions effect on reaction was considered; Imidazolium ionic liquids share in the solution of 6% mass fraction of the time, which has a better catalytic activity. At this time the yield of obtained product was 76%, 73%, 70% respectively; (5) Mechanism on Claisen-Schmidt condensation between 6- methoxy-2-naphthalene and acetone was also discussed in the article.