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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (12): 2017-2020. 上一篇    下一篇

研究简报

盘状液晶中间体单羟基苯并菲简便合成

赵可清*；杨高帆；余文浩；汪必琴；胡 平   

  1. (四川师范大学化学与材料科学学院 成都 610066 )
  • 收稿日期:2009-04-28 修回日期:2009-07-15 发布日期:2009-07-15
  • 通讯作者: 赵可清 E-mail:zhaokeqing@yahoo.com.cn; kqzhao@sicnu.edu.cn
  • 基金资助:

    国家级.国家自然科学基金

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

Zhao, Keqing*；Yang, Gaofan；Yu, Wenhao；Wang, Biqin；Hu, Ping   

  1. (College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610066)
  • Received:2009-04-28 Revised:2009-07-15 Published:2009-07-15

PDF

2254

被引次数

13

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%.

关键词: 盘状液晶, 苯并菲, 羟基苯并菲, 选择性脱甲基

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 trimerization of 1,2-dialkoxybenzene and 2-methoxyphenol by FeCl3 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%.

Key words: discotic liquid crystal, triphenylene, 2-hydroxy-3-methoxy-6,7,10,11-tetra-(alkoxy)tripheny- lene, 2-hydroxy-3,6,7,10,11-penta(alkoxy)triphenylene, selective demethylation