摘要
本文报道6-氯-1,4-二氢-1,4-环氧萘(1)的合成与表征。以4-氯-2-碘苯酚(2)为原料,首先经过羟基保护得到4-氯-2-碘苯基-4-甲基苯磺酸酯(3),然后在异丙基溴化镁作用下原位生成苯炔中间体,再和呋喃发生Diels-Alder反应得到目标化合物(1),中间体及产物结构经核磁共振氢谱、碳谱和质谱表征。并重点讨论影响产物(1)收率的主要因素,确定最佳反应条件为:物料摩尔比n_(呋喃)∶n3=6∶1;异丙基溴化镁的最佳的用量为ni-PrMgBr∶n3=1.3∶1。在最佳合成条件下,6-氯-1,4-二氢-1,4-环氧萘(1)的收率达到66.5%。
The synthesis and characterization of 6-chloro-1,4-dihydro-1,4-epoxynaphthalene(1)was reported.Using 4-chloro-2-iodophenol(2)as starting material,4-chloro-2-iodophenyl-4-methylbenzenesulfonate(3)was firstly obtained by hydroxyl protection,and then the benzyne intermediate was synthesized in situ by the reaction of i-PrMgBr,the target compound(1)was obtained by Diels-Alder reaction with Furan.The structure of the intermediate and the product were characterized by 1H NMR,13C NMR and MS.The main factors affecting the yield of product(1)were discussed.The optimum reaction conditions were determined as follows:the molar ratio of n_(furan)∶n3=6∶1;the dosage of i-PrMgBr was ni-PrMgBr∶n3=1.3∶1.Under the optimum conditions,the yield of 6-chloro-1,4-dihydro-1,4-epoxynaphthalene(1)was up to 66.5%.
作者
徐小娜
王晓霞
李祯
柯苗
仝红娟
XU Xiao-na;WANG Xiao-xia;LI Zhen;KE Miao;TONG Hong-juan(School of Pharmaceutical&Chemical Engineering,Xianyang Vocational Technical College,Xianyang 712000,China;Collaborative Innovation Center of Green Manufacturing Technology for Traditional Chinese Medicine in Shaanxi Province,School of Pharmacy,Shaanxi Institute of International Trade&Commerce,Xi'an 712046,China)
出处
《化学工程师》
CAS
2021年第10期11-14,共4页
Chemical Engineer
基金
咸阳职业技术学院博士科研基金项目(No.2021BK01)
咸阳职业技术学院科学研究基金资助项目(No.2020KJB02)。
