第 37 卷第 2 期 | ![](image2/wentou.gif) | Vol. 37 No. 2 | 2007 年 4 月 | Apr 2007 |
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所属栏目:农药及中间体
6,11-二氢二苯骈[b,e]氧杂 -11-酮-2-乙酸的合成 |
汪 淼,杨艺虹,张 珩,杨建设,吴春姗
(武汉工程大学 湖北省新型反应器与绿色化学工艺重点实验室,湖北 武汉 430073) |
摘 要:采用对羟基苯乙酸(Ⅱ)和苯酞为原料,在甲醇钠的催化下,以n(Ⅱ) ∶ n(苯酞) ∶ n(甲醇钠)=1.0 ∶ 1.1 ∶ 2.2,于130℃反应7 h制备4-(2-羧基苄氧基)苯乙酸(Ⅲ)。Ⅲ与乙酰氯经氯化、环合得6,11-二氢二苯骈[b,e]氧杂 -11-酮-2-乙酸(Ⅰ),该步优化的反应条件为:n(Ⅲ) ∶ n(乙酰氯)=1 ∶ 1.25,反应温度为100℃,反应时间为6 h。以Ⅱ计,总收率达48.16%,Ⅰ的结构经IR、1H NMR和MS确证。 |
关键词:对羟基苯乙酸;苯酞;4-(2-羧基苄氧基)苯乙酸;环合 |
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Synthesis of 6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-acetic Acid |
WANG Miao,YANG Yi-hong,ZHANG Heng,YANG Jian-she,WU Chun-shan
(Hubei Key Laboratory of Novel Chemical Reactor & Green Chemical Technology,Wuhan Institute of Technology,Wuhan 430073,China) |
Abstract:4-(2-Carboxybenzyloxy)phenylacetic acid (Ⅲ)was synthesized from 4-Hydroxyphenyl acetic acid(Ⅱ)and phthalide in the presence of the catalyst sodium methoxide. The molar ratio of reactants(Ⅱ ∶ phthalide ∶ sodium methoxide)was 1.0 ∶ 1.1 ∶ 2.2,the reaction time was 7 h and reaction temperature was 130℃. 6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid(Ⅰ) was synthesized from Ⅲand acetyl chloride through two-step reactions including chlorination and cyclization. The optimum reaction conditions were as follows:n(Ⅲ) ∶ n(acetyl chloride)=1 ∶ 1.25,reaction time 6 h and reaction temperature 100℃. The overall yield that was calculated from Ⅱ was 48.16%. Structure of Ⅰ was characterized by IR,1H NMR and MS. |
Key words:4-hydroxyphenyl acetic acid;phthalide;4-(2-carboxybenzyloxy)phenylacetic acid;cyclization |
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作者简介:汪 淼(1982-),女,湖北宜昌人,硕士研究生,主要从事药物合成研究。(E-mail:wangmiao_911@163.com)
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联 系 人:杨艺虹(1954-),女,教授,硕士生导师,主要从事制药工程专业教学及药物研究工作。
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收稿日期:2007-01-13
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