Synthesis Of Intermediate Of Leaf Alcohol--β-Acetylacrylic Acid

Leaf alcohol, systematically named cis-3-hexen-l-ol,is a kind of natural perfume, existing in the leaves and fruits of green plants. It can not be only added in soft drinks, cold beverages and candy as eatable perfume, but also used to prepare various kinds of flower-smelling essence and man-made oil. In addition, leaf alcohol can be used to synthesize multi-kinds of kairomone.Organometallic compounds are widely used in synthetic chemistry. The Grignard reagent are usually used to prepare many compounds such as alcohol, alkane, ester etc. Organozinc reagent and organocadmium reagent are widely used in synthesizing ketones and asymmetric ketones. For example, the Blaise reaction in which ketone is prepared by organocadmium and acylchlorine and the Gilman-Nelson reaction in which asymmetric ketone is prepared by organocdmium and acylhalide.In this paper, the synthesis of cis- β -acetylacrylic acid-intermediate of leaf alcohol has been studied. Organometallic compounds which made by ourselves through Grignard reagent and cadmium chloride is used to react with Maleic anhydride to prepare cis- β -acetylacrylic acid. In this way, the feasibility of multi-step synthetic method of leaf alcohol through cycloreversion of Maleic anhydride has been discussed. A systematic study on the influence of several factors such as reaction time , reaction temperature , solvent volume and component ratio on the yield has been made. In this experiment, the yield is calculated by UV analysis method, the product is separated and purified by ion exchange technology, the purity is measured by the electricity titration method, at last, the structure is validated by UV,FTIR and HNMR. This paper also reports our investigations and researches of orthogonal experiment that explains in a systematic way the interaction of pre-factors and gives preliminary analysis on the mechanism of reaction. Through a series of experiments, a conclusion can be drew that the method which synthesize cis-β -acetylacrylic acid from Maleic anhydride is feasible.