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%.