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Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (12): 2017-2020. Previous Articles     Next Articles

Reviews

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

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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