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

作者：Zhao Keqing^*; Yang Gaofan; Yu Wenhao; Wang Biqin; Hu Ping

来源：Chinese Journal of Organic Chemistry, 2009, 29(12): 2017-2020.

• discotic liquid crystal
• triphenylene
• 2-hydroxy-3-methoxy-6,7,10,11-tetra-(alkoxy)triphenylene
• 2-hydroxy-3,6,7,10,11-penta(alkoxy)triphenylene
• selective demethylation

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 FeCl(3) 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 Ph(2)PLi afforded the title compounds. The total yield of the three steps was in the range of 14%similar to 19%.

• 出版日期2009-12
• 单位四川师范大学