The Synthesis And Application Of Decaprenol

In this thesis,we mainly research the synthesis of solanesyl bromide, solanesyl ethyl acetoacetate, solanesyl acetone, and 1-solanesyl-2-ethynyl-2-propanol, from which we can make up the path to synthesize decaprenol from solanesol .Otherwise, we improve the reaction elements such as solvent and temperature, the detection and the purification of solanesyl bromide.In the molar ratio of 1:1.5, solanesol(90%) was treated with PBr3 in -5～0℃, catalyzed by pyridine,which afforded a good yield of 68.5%.Then, solanesyl bromide reacted with the cooresponding sodium salt of acetacetic ester in the molar ratio of 1:1.5 at 40℃, the yield of solanesyl acetone was 90.9%. After saponification and ketonic decarboxylation, solanesyl acetone was totally converted to solanesyl acetone.Finally, Stirring the solution of sodium acetylide and solanesyl acetone for 6h at different temperatures, the nucleophilic addition did not take place, we failed to receive the anticipated 1-solanesyl-2-ethynyl-2-propanol.All the products have been identified by by MALDI-FTMS.Synthesizing decaprenol from solanesyl bromide, solanesyl acetone, and 1-solanesyl-2-ethynyl-2-propanol is not in commone use, only a few papers reported the methed vaguely. Our work is to grope for the concrete reaction conditons of this method. After plenty of experiment, we think it is a viable way which can be industrialized.