Magnesium oxide as a heterogeneous and recyclable base for the N-methylation of indole and O-methylation of phenol using dimethyl carbonate as a green methylating agent

被引:34
|
作者
Gadge, Sandip T. [1 ]
Mishra, Ashish [1 ]
Gajengi, Aravind L. [1 ]
Shahi, Nileshkumar V. [1 ]
Bhanage, Bhalchandra M. [1 ]
机构
[1] Inst Chem Technol, Dept Chem, Bombay 400019, Maharashtra, India
关键词
ALKYLATION; DIMETHYLCARBONATE; CHEMISTRY; METHANOL;
D O I
10.1039/c4ra07240e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This work reports a mild efficient and sustainable protocol for N-methylation of indole and O-methylation of phenol using dimethylcarbonate as an environmentally safe, non-toxic, biodegradable and green methylating agent under microwave conditions. Magnesium oxide (MgO) has been employed as a heterogeneous and recyclable base for clean N-methylation of indole and O-methylation of phenol with dimethylcarbonate. Basic properties of the fresh and recycled MgO were measured by temperature programmed desorption (CO2-TPD) analysis. The CO2-TPD runs suggested that both strong and moderately basic sites are present on the oxide, while only the moderately basic sites are responsible for the N-and O-methylation of indole and phenol, respectively, using DMC as a methylating agent. The CO2-TPD analysis showed that the basic sites on fresh and recycled MgO were comparable. The MgO was isolated by simple filtration and recycled efficiently without loss in activity and selectivity.
引用
收藏
页码:50271 / 50276
页数:6
相关论文
共 24 条
  • [1] High performance method for O-methylation of phenol with dimethyl carbonate
    Ouk, S
    Thiébaud, S
    Borredon, E
    Le Gars, P
    APPLIED CATALYSIS A-GENERAL, 2003, 241 (1-2) : 227 - 233
  • [2] Copper-Catalyzed N-Methylation of Amides and O-Methylation of Carboxylic Acids by Using Peroxides as the Methylating Reagents
    Xia, Qinqin
    Liu, Xiaolong
    Zhang, Yuejiao
    Chen, Chao
    Chen, Wanzhi
    ORGANIC LETTERS, 2013, 15 (13) : 3326 - 3329
  • [3] Single-Step Methylation of Chitosan Using Dimethyl Carbonate as a Green Methylating Agent
    Hemming, Ellen B.
    Masters, Anthony F.
    Perosa, Alvise
    Selva, Maurizio
    Maschmeyer, Thomas
    MOLECULES, 2019, 24 (21):
  • [4] O-methylation of natural phenolic compounds based on green chemistry using dimethyl carbonate
    Prakoso, N. I.
    Pangestu, P. H.
    Wahyuningsih, T. D.
    10TH JOINT CONFERENCE ON CHEMISTRY, 2016, 107
  • [5] N-methylation of Benzylamine to N,N-dimethylbenzylamine by Using Dimethyl Carbonate as a Methylation Agent over Aluminophosphate Molecular Sieves
    Zhu, Maodian
    Liu, Shaoying
    Wang, Gongying
    EKOLOJI, 2019, 28 (107): : 1451 - 1461
  • [6] SELECTIVE O-METHYLATION OF PHENOL WITH DIMETHYL CARBONATE OVER X-ZEOLITES
    FU, ZH
    ONO, Y
    CATALYSIS LETTERS, 1993, 21 (1-2) : 43 - 47
  • [7] Selective O-Methylation of Phenol with Dimethyl Carbonate over Catalysts Supported on CaO
    Zhifang Zhang
    Zhongying Xu
    Shaoying Li
    Shijun Chen
    Ying Tang
    Kinetics and Catalysis, 2021, 62 : 496 - 506
  • [8] Selective O-Methylation of Phenol with Dimethyl Carbonate over Catalysts Supported on CaO
    Zhang, Zhifang
    Xu, Zhongying
    Li, Shaoying
    Chen, Shijun
    Tang, Ying
    KINETICS AND CATALYSIS, 2021, 62 (04) : 496 - 506
  • [9] A practical method for N-methylation of indoles using dimethyl carbonate
    Jiang, XL
    Tiwari, A
    Thompson, M
    Chen, ZH
    Cleary, TP
    Lee, TBK
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (06) : 604 - 608
  • [10] Light-assisted O-methylation of phenol with dimethyl carbonate over a layered double oxide catalyst
    Wang, Xiaoyu
    Wang, Ruiyi
    Gu, Xianmo
    Jia, Jianfeng
    Zheng, Zhanfeng
    CATALYSIS SCIENCE & TECHNOLOGY, 2019, 9 (08) : 1774 - 1778