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邻三甲氧基苯类化合物的选择性去甲基化反应研究
引用本文:曾启华,张素英,徐中轩,赵光练,张海.邻三甲氧基苯类化合物的选择性去甲基化反应研究[J].合成化学,2017,25(2).
作者姓名:曾启华  张素英  徐中轩  赵光练  张海
作者单位:1. 遵义师范学院化学化工学院,贵州遵义 563002;贵州省黔北特色资源应用研究实验室,贵州遵义 563002;2. 遵义师范学院化学化工学院,贵州遵义,563002
基金项目:贵州省教育厅"125"重大科技专项
摘    要:以溴化氢为催化剂,冰醋酸为溶剂,邻三甲氧基苯类化合物(1a~1f)为原料,于室温经选择性去甲基化反应合成了一系列丁香酸衍生物,其结构经~1H NMR和MS(ESI)确证。以丁香酸(2a)的合成为例,优化了合成条件。结果表明:在最佳反应条件(1 1 mmol,33%HBr 0.35 mL,冰醋酸0.5 mL,于室温反应24 h)下,2收率58%~85%。2a的放大合成收率为75%。

关 键 词:选择性去甲基化  邻三甲氧基苯  合成  丁香酸  放大实验

Research on Selective Demethylation of Trimethoxybenzene Compounds
ZENG Qi-hua,ZHANG Su-ying,XU Zhong-xuan,ZHAO Guang-lian,ZHANG Hai.Research on Selective Demethylation of Trimethoxybenzene Compounds[J].Chinese Journal of Synthetic Chemistry,2017,25(2).
Authors:ZENG Qi-hua  ZHANG Su-ying  XU Zhong-xuan  ZHAO Guang-lian  ZHANG Hai
Abstract:A serial of syringic acid derivatives were synthesized by the reaction of regioselective dem-ethylation of trimethoxybenzene compounds at rt, using hydrogen bromide as catalyst and AcOH as sol-vent. The structures were confirmed by 1 H NMR and MS( ESI) . The synthesis reaction conditions were optimized, using 2a as example. The results indicated that under the optimum conditions(11 mmol, 33%HBr 0. 35 mL, AcOH 0. 5 mL, reaction at rt for 24 h), the yields of 2 were 58% ~85%, re-spectively. The amplification scale experiment of synthesis 2a can also obtained in yield of 75%.
Keywords:regioselective demethylation  trimethoxybenzene  synthesis  syringic acid  amplification scale experiment
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