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3-香叶基-2,4,5-三甲氧基苯甲酸甲酯的合成

Synthesis of Methyl 3-Geranyl-2,4,5-trimethoxybenzoate

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【作者】 周北斗; 童玉贵; 阮志鹏; 许桂芬;

【Author】 ZHOU Beidou;TONG Yugui;RUAN Zhipeng;XU Guifen;School of pharmacy and medical technology,Putian university;Putian entry-exit inspection and quarantine bureau;

【机构】 莆田学院药学与医学技术学院; 莆田出入境检验检疫局;

【摘要】 以2,4,5-三甲氧基苯甲醇作为起始原料,经过叔丁基二甲基氯硅烷保护苄位羟基、香叶基的选择性取代、脱除硅保护基、沙瑞特试剂氧化苄位羟基成醛基、亚氯酸钠氧化醛基成羧基和甲酯化反应制得目标分子3-香叶基-2,4,5-三甲氧基苯甲酸甲酯。各中间体和目标分子都经核磁共振氢碳谱、红外光谱和高分辨质谱确证结构。六步总产率为31%。

【Abstract】 The synthesis of methyl 3-geranyl-2,4,5-trimethoxybenzoate was investigated.2,4,5-Trimethoxybenzyl alcohol was employed as the starting material.Then target molecule was obtained via protection of hudroxy group employing tert-butyldimethylsilyl chloride,selective alkylation of benzene ring on the C-3position with geranyl bromide,deprotection of sily group,conseculative oxidation of benzylic hydroxy group by Sarett reagent and sodium chlorite respectively and finally methyl esterification reaction.The structures of all the intermediates and target compound were confirmed by 1 H NMR,13 C NMR,IR and HRMS spectra.The total yield of six steps was 31%.

【关键词】 香叶基; 苯甲酸甲酯; 合成;
【Key words】 geranyl; methyl benzoate; synthesis;
【基金】 福建省中青年教师教育科研项目(JA15453);莆田市科技计划项目[2014S02(3)];莆田学院科研项目(2014053,2015076)
  • 【文献出处】 南昌大学学报(理科版) ,Journal of Nanchang University(Natural Science) , 编辑部邮箱 ,2017年01期
  • 【分类号】TQ245.24
  • 【下载频次】133
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