Synthesis Of Spiro[furan-2(3H),5’-[4,7]methano[5H]indene]

As a new kind of top-grade fragrance, Spiro[furan-2(3H),5’-[4,7]methano[5H]Ind--ene] is widely used in the flavorings of shampoo,soap,anti perspirant and other cosmetics,and it has broad market propects.The article mainly studies the synthesis process of the Spiro[furan-2(3H),5’-[4,7]methano[5H]indene] and the investigates relative factors influence on reaction including catalyst,reaction temperature,reaction time,material matching and other fators.The optimal reaction condition was determined and the technological parameters of industrial production were offered.In this thesis,starting from dicyclopentadiene,intermediates cyclopentanonorcam--phor was synthesized by the reaction of hydration,hydrogenation and oxidation,then through Wittig reaction with the phosphine ylide reagent of3-bromo-l-propanol, olefinic alcohol cyclization to abtain Spiro[furan-2(3H),5’-[4,7]methano[5H]indene].The technological conditions was improved and optimized.Hydration is run at a temperature of105℃for5.5hours with25%sulfuric acid,the mass ratio of cyclopentanonorcamphor and sulfuric acid is1:1.Hydrogenation is run at a temperature of95℃for4hours with5%Pa/C as catalyst,the pressure was controlled between3.5MPa to4.0MPa.Oxidation is run at a temperature of80℃for5hours with50%H2O2as oxidant,sodium tungstate as catalyst and trioctylmethylammonium chloride as phase transfer catalyst,the molar ratio of hydrogenated product and H2O2isl:3.The Wittig reaction is run at a temperature of10-15℃for3.5hours with tetrahydrofuran as solvent,the molar ratio of cyclopentanonorcamphor and the phosphine ylide reagent of3-bromo-1-propanol is1:1.Olefinic alcohol cyclization is run at room temperature for30min with dichloromethane as solvent,the molar ratio of methanesulfonic acid and4-(Tricyclo-[5.2.1.02,6]-decyl-8-indene)propanol is2:1.In this thesis,a new path of synthesizing Spiro[furan-2(3H),5’-[4,7]methano[5H]--indene] was designed.The advantages of the procedure are easy operation,mild reaction conditions and low costs,so it can be expected to have a good prospect for industrial application.The structures of the product and the intermediate compounds were identified by IR,1HNMR analysis.The overall yield of5steps reaction was over35%.