3-氯-2-羟基-环己-2-烯酮的合成

Synthseis of 3-chloro-2-hydroxy-cyclohex-2-enone

以2-氯环己酮为原料,与亚硝酸异戊酯在盐酸甲基叔丁基醚溶液中室温反应,得到3-氯-2-羟基-环己-2-烯酮肟(3),再经HCl水解得到3-氯-2-羟基-环己-2-烯酮(1),在石油醚中结晶得纯品。产物结构经1H NMR确证。优化了反应条件:羟胺化反应中,甲基叔丁基醚为溶剂;n2-氯环己酮∶n亚硝酸异戊酯=1∶1.2;室温反应40min;水解反应中,HCl浓度为2N;反应温度40℃。优化条件下总收率40.9%,产物纯度>99%。合成途径简捷、条件温和、后处理简单、总收率高,产品质量好。

Using 2-chlorocyclohexanone as raw material,reacted with isoamyl nitrite in HCl methyl tert-butyl ether solution at room temperature,to obtained 3-chlorine-2-hydroxy-cyclohexane-2-ketenone oxime(3),and then(3)was hydrolyzed in HCl solution to obtained 3-chlorine-2-hydroxy-cyclohexane-2-ketenone(1),which was crystallized in petroleum ether.The structure of the product was confirmed by 1H NMR.The reaction conditions were optimized:in hydroxylamination,methyl tert-butyl ether as the solvent;n2-chlorocyclohexanone∶niso-amyl nitrite=1∶1.2;Reaction at room temperature for 40min.In the hydrolysis reaction,the concentration of HCl solution was 2N;The reaction temperature is 40℃.Under optimal conditions,the total yield was 40.9%and the purity of the product>99%.The synthetic method is simple,the condition is mild,the work-up is simple,the total yield is high,the product quality is good.