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Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (12): 2017-2020. Previous Articles Next Articles
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赵可清*;杨高帆;余文浩;汪必琴;胡 平
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国家级.国家自然科学基金
Zhao, Keqing*;Yang, Gaofan;Yu, Wenhao;Wang, Biqin;Hu, Ping
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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
DIAO Ge-Qing, YANG Gao-Fan, TU Wen-Gao, HONG Bi-Qin, HU Beng. Simple Synthetic Method for Discotic Liquid Crystal Intermediates: 2-hydroxy-3,6,7,10,11-penta(alkoxy)triphenylenes[J]. Chin. J. Org. Chem., 2009, 29(12): 2017-2020.
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