[1]张启蒙,金长春,陈　群,等.2 - 硝基- 5 - 苄氧基甲苯的合成[J].常州大学学报(自然科学版),2007,(01):1-4.
　ZHAN G Qi - meng,J IN Chang - chun,CHEN Qun,et al.Study of Phase Transfer Catalytic Synthesis of 5 - Benzyloxy - 2 - Nitrotoluene[J].Journal of Changzhou University(Natural Science Edition),2007,(01):1-4.
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2 - 硝基- 5 - 苄氧基甲苯的合成()
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常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
期数:
2007年01期
页码:
1-4
栏目:
出版日期:
2007-03-25

文章信息/Info

Title:
Study of Phase Transfer Catalytic Synthesis of 5 - Benzyloxy - 2 - Nitrotoluene
作者:
张启蒙1; 2 ;  金长春1 ;  陈　群2 ;  陈智栋1
1 江苏工业学院化学工程系, 江苏 常州 213164 ; 2.常州工程职业技术学院化学工程系, 江苏 常州 213164
Author(s):
ZHAN G Qi - meng1; 2 ;  J IN Chang - chun1 ;  CHEN Qun2 ;  CHEN Zhi - dong1
1. Department of Chemical Engineering , J iangsu Polytechnic Univer sity , Changzhou 213164 , China ; 2. Department of Chemical Engineering , Changzhou Instit ute of Engineering Technology , Changzhou 213164 , China
关键词:
4 - 硝基间甲酚;  2 - 硝基- 5 - 苄氧基甲苯;  聚乙二醇600 ;  硝化;  醚化
Keywords:
4 - nit ro - m - cresol ;  5 - benzyloxy - 2 - nit rotoluene ;  PEG- 600 ;  nit ration ;  et herification
分类号:
O 625. 61
文献标志码:
A
摘要:
2 - 硝基- 5 - 苄氧基甲苯是有机中间体, 可以进一步采用Reissert 法合成吲哚类化合物。以间甲酚为原料, 采用一步硝 化法, 先0 ℃以下亚硝化, 再程序升温至45 ℃氧化得到4 - 硝基间甲酚粗品。产品精制后收率为7615 % , 高于两步硝化法的收 率52 %。探索了苄基三乙基氯化铵、四丁基溴化铵、OP - 10 、聚乙二醇200 和聚乙二醇600 等几种相转移催化剂对该步反应 收率的影响。聚乙二醇600 的相转移催化作用明显, 精制后产品收率在89 %以上。4 - 硝基间甲酚与氯化苄在乙醇钠作催化剂 的条件下制备2 - 硝基- 5 - 苄氧基甲苯, 收率为861 9 %。合成2 - 硝基- 5 - 苄氧基甲苯的总收率达77 %以上。通过熔点、红 外和气质联用对产品进行了表征。
Abstract:
The 5-benzyloxy -2- nitrotoluene is an organic intermediate to prepare indoles by Reissert indole synthesis. 4 - Nitro - m -cresol was synt hesized from m -cresol by means of one - step nit ration , firstly nitrosation at the temperature lower than 0 ℃, then oxidation at 45 ℃ by means of programmed temperat ure. The yield of 4 - nit ro- m- cresol after purification was 76.5 % higher than two - step nit ration which was 52 %. Benzyl t riethyl ammonium chloride , tet rabutyl ammonium bromide , OP - 10 , polyet hylene glycol 200 , polyet hylene glycol 600 , etc. , these phase transfer catalysts′effect on the yield of this step was researched. Polyet hylene glycol 600 showed good phase transfer catalytic effect ; the yield after purification was above 89 %. 4 - Nitro - m- cresol and benzyl chloride , with sodium et hylate as the catalyst , synt hesized 5 - benzyloxy - 2 - nit rotoluene , the yield was 86.9 %. The overall yield of the synt hesis of 5 - benzyloxy - 2 - nit rotoluene was above 77 %. The product was characterized by melting point , IR and GC - MS.

参考文献/References:

[1] 花文廷1 杂环化学[M] 1 北京: 北京大学出版社, 19911236 - 243.
[2] 周卫, 胡惟孝, 杨忠愚1 5 - 取代吲哚类化合物的合成[J] 1 合成化学, 2002 , 3 : 200 - 2051
[3] Michael E F , Thomas A C , J ames A C. Synt hesis and evalua2 tion of t he antiovulatory activity of a variety of melatonin analoues [J] . J Med Chem , 1979 , 22 (1) : 63 - 64.
[4] 蒋培华, 顾寿胜, 徐俊伟1 3 - 甲基- 4 - 硝基苯甲醚的合成 [J] 1 精细石油化工进展, 2004 , 5 (1) : 39 - 40.
[5] 王国喜, 彭聪虎1 5 - 甲氧基吲哚的合成[J] 1 应用化学, 2002 , 19 (10) : 1 014 - 1 015.
[6] Batcho A D , Leimgruber W. Intermediates for indoles [P] . US : 3976639 , 1976 - 08 - 24.
[7] 赵奇飞, 梁兴俭, 张伟, 等1 药物体P - 氨基苯基苄基醚的合 成研究[J] 1 天津理工学院学报, 2000 , 16 (1) : 83 - 85.
[8] 陈红艳, 胡伟武1 聚乙二醇催化合成甲基异柳磷[J] 1 应用 化工, 2004 , 33 (3) : 15 - 17.
[9] 王亚飞, 陈宝玉, 毕红梅, 等1 聚乙二醇催化肉桂醛合成方法 [J] 1 佳木斯大学学报, 2004 , 22 (4) : 505 - 507.

备注/Memo

备注/Memo:
作者简介: 张启蒙(1979 - ) , 女, 江苏南通人, 硕士研究生。
更新日期/Last Update: 2007-03-25