A Study On The Synthesis Of Ferulic Acid And Its Derivatives

Ferulic acid is one kind of phenolic acid, which has popular physiological characteristics and pharmacological effects, it has been applied in antithromc,antitumor, anti-anging, enhance of human immunity and other areas. In the molecular structure of ferulic acid, due to its own existence of hydrophilic hydroxyl and relatively short chain alkanes, makes its fat-soluble bad. thus its application is limited.this paper introduces the synthesis of ferulic acid and acetylferulic acid. Then a various of derivatives of ferulic acid were prepared by esterification reaction. such as:acetylferuloyl chloride, menthol acetylferulate, borneol ester acetylferulate and geraniol ester ferulate. the compounds above were characterized and the structures of the products were determined.(1) Acetylferulic acid was synthesized by vanillin and acetic anhydride under Perkin reaction, catalyzed by sodium acetate trihydrate, the yield rate was 88.6%.Ferulic acid was prepared after hydrolysis and acidification, the yield rate was 72.0%.The optimum synthetic process condition of acetylferulic was obtained through single-factor experiment and orthogonal experiment. The structures of the products were characterized and determined through Micro melting point instrument, Fourier Transform Infrared Spectrometer(FT-IR), Superconducting Nucleus Magnetic Resonance Spectrometer(1H NMR, 13CNMR).(2)Acetylferulic acid and thionyl chloride were used as the raw materials to prepare acetylferuloyl cholide. then menthol acetylferulate and bomeol ester acetylferulate were synthesized by acetylferuloyl chloride, natural alcohol (menthol, borneol) and sodium tripolyphosphate. the yields of the two compounds were 78.5% and 74.2%.The optimum synthetic process condition of menthol acetylferulate was obationed through single-factor experiment and orthogonal experiment. The structures of the two products were characterized and determined through Fourier Transform Infrared Spectrometer(FT-IR),Superconducting Nucleus Magnetic Resonance Spectrometer(1H NMR, 13CNMR).(3) geraniol ester ferulate was synthesized with ferulic acid and geraniol under the catalytic of p-toluene sulfonic acid by microwave irridiation. the yield of the target compound was 71.2%. The optimum synthetic process condition of geraniol ester ferulate was obtained by single factor experiment and orthogonal experiment. The structure of the target compound was characterized and determined through the Fourier Transform Infrared Spectrometer(FT-IR), Superconducting Nucleus Magnetic Resonance Spectrometer(1H NMR,13CNMR).