盘状液晶中间体单羟基苯并菲简便合成  

A Simple Synthetic Method for Discotic Liquid Crystal Intermediates:2-Hydroxy-3,6,7,10,11-penta(alkoxy)triphenylenes

作　　者：赵可清[1] 杨高帆[1] 余文浩[1] 汪必琴[1] 胡平[1] 

机构地区：[1]四川师范大学化学与材料科学学院,成都610066

出　　处：《有机化学》2009年第12期2017-2020,共4页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.50673069;50811140156)资助项目

摘　　要：羟基苯并菲[TP(OH)(OR)5]是一类重要的盘状液晶中间体.根据苯并菲衍生物间极性差异,设计了一条简便的合成与分离羟基苯并菲的方法:在70%硫酸中用FeCl3氧化邻苯二醚与2-甲氧基苯酚三聚成环,分离获得2,3,6,7,10,11-六烷氧基苯并菲[TP(OR)6]和2-羟基-3-甲氧基-6,7,10,11-四烷氧基苯并菲[TP(OH)(OMe)(OR)4].后者再经醚化,Ph2PLi脱甲基得2-羟基-3,6,7,10,11-五烷氧基苯并菲[TP(OH)(OR)5].三步反应总收率14%～19%.Monohydroxytriphenylene [TP（OH）（OR）5] is an important intermediate for functionalized or polymeric discotic liquid crystals. Based on the polarity difference among triphenylene derivatives, a new simple method was designed to synthesize monohydroxytriphenylene [TP（OH）（OR）5]： oxidative trimeriza- tion of 1,2-dialkoxybenzene and 2-methoxyphenol by FeC13 in 70% sulfuric acid resulted in 2,3,6,7,10,11-hexa（alkoxy）triphenylene [TP（OR）6] and 2-hydroxy-3-methoxy-6,7,10,11-tetra（alkoxy）triphenylene [TP（OH）- （OMe）（OR）4], then alkylation with RBr and demethylation with Ph2PLi afforded the title compounds. The total yield of the three steps was in the range of 14%- 19%.

关 键 词：盘状液晶 苯并菲 2-羟基-3-甲氧基-6 7 10 11-四烷氧基苯并菲 2-羟基-3 6 7 10 11-五烷氧基苯并菲 选择性脱甲基 

分 类 号：O753.2[理学—晶体学]