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《Chemical Reagents》 2011-10
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An improvement of the synthesis for 1-nitro-cyclohexene

XU Hai-yun,FENG Cui-lan (Department of Chemistry,Shangqiu Normal College,Shangqiu,476000,China)  
Cyclohexene was obtained by dehydration of cyclohexanol using mixed acid composed of concentrated sulfuric acid and phosphoric acid as catalyst,and when the volume ratio of concentrated sulfuric acid to phosphoric acid in the mixed acid was 1:2,the yield of cyclohexene was maximal.1-nitrocyclohexene was prepared by nitration reaction of cyclohexene with sodium nitrite and iodine in ethyl acetate and water in the presence of ethylene glycol(EG),and its structure was characterized by 1HNMR,IR and elemental analysis.The appropriate reaction conditions at room temperature were as follows:cyclohexene was 24 mmol and iodine was 36 mmol,n(NaNO2)∶n(cyclohexene) was 6.0∶1.0,n(EG)∶n(cyclohexene) is 2.5~3.0 and the reaction time was 72 h,and the yield of 3 was 65.7% under the conditions.The one-pot synthetic method for obtaining 1-nitrocyclohexene,which employed I2-CH2OHCH2OH/NaNO2 instead of HgCl2/NaNO2 to nitrify cyclohexene,was not involved in handling the intermediate with basic solution,with avoiding using of the highly toxic reagents,and its pretreatment process was simple and convenient due to its homogeneous reaction system,along with higher yield.
【Fund】: 河南省科技厅科技攻关项目(082102210050);; 河南省教育厅自然科学研究计划项目(2008B150018);; 河南省教育厅自然科学研究资助计划项目(2011A150023);; 商丘师院重大项目培育计划立项项目(2011ZDPY02);; 安徽省高校自然科学基金项目(KJ2007B093)
【CateGory Index】: TQ236
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