Study On Purification Of Solanesol And Synthesis Of Vitamin K₂

Solanesol has a good effect on anti-bioaction、anti-bacterium and diminishing inflammation, which is an important intermediate of producing CoQ10、Vitamin K2and SDB. It has a good application prospect.The special pharmacological effect of Vitamin K2is paid more attention with the development of modern medicine, but its application and improvement are hindered on account of higher cost for its biological extraction. So it is being attached more and more importance that how to develop a chemical method to synthesize Vitamin K2and put it into industrialization.Using15%solanesol as raw material, and it was saponificated with acetone and methanol at40℃. The liquid reaction mixture cooled0℃and separated out solid. The purity of product analyzed by HPLC was66%and the molar yield is70.1%.On the basis of the dicyclopentadiene of the monomerization, under170～200℃, cracking cyclopentadiene fraction, the purity of product analyzed by GC was96.7%and the molar yield is70%. 1,4,4a,9a-tetrahydro-9aa-methyl-1α,4α-methanoanthraquinone was synthesized by catalytic of2-methyl-1,4-naphthoquinone and cyclopentadiene in presence of lewis acid and protonic acids. The optimum reaction conditions were as follows:the reaction temperature was30℃, the catalyst boron trifluoride etherate dosage was4mL by weight of the2-methyl-1,4-naphthoquinone and the dosage of the cyclopentadiene was4mL per1g2-methyl-1,4-naphthaquinone. The reaction temperature was35℃and the reaction time was4hour when the catalyst was acetic acid. The catalyst boron trifluoride etherate and acetic acid made the cost relatively lower and the reation efficiency higher.Hexane dissolved60%solanesol as raw material, to which a solution of phosphorus tribromide in hexane was added dropwise at-10℃, the resultant mixture was stirred for1.5hours at0-5℃, the liquid reaction mixture was added into ice water to make extraction twice with potroleum ether (30～60℃).1,4,4a,9a-tetrahydro-9aα-methyl-4aa-solanesyl-1α,4α-methanoanthraquin one can be obtained by the deprotonaton of1,4,4a,9a-tetrahydro-9aa-methyl-la,4a-methanoanthraquinone with potassium t-butoxide, and then alkylation with solanesyl bromide.The resultant solution was reacted at0℃in an argon stream. The molar yield was69.3%based on1,4,4a,9a-tetrahydro-9aa-methyl-1a,4a-methanoanthraquinone.The purity of product after treatment was higher and the luster was fine when retro-Diels-Alder reaction of shorter duration was in100℃for1hour with toluene as solvent. The molar yield was90.3%based on1,4,4a,9a-tetrahydro-9aa-methyl-4aa-solanesyl-1a,4α-methanoanthraquinone.This method had the advantage of equipment simple, workable, low-cost and easy industrialization.