A Convenient and "Greener" Synthesis of Methyl Nitroacetate

被引:4
|
作者
Johnson, Eric C. [1 ]
Guzman, Pablo E. [1 ]
Wingard, Leah A. [1 ]
Sabatini, Jesse J. [1 ]
Pesce-Rodriguez, Rose A. [2 ]
机构
[1] US Army, Energet Technol Branch, Res Lab, Aberdeen Proving Ground, MD 21005 USA
[2] US Army, Energet Mat Sci Branch, Res Lab, Aberdeen Proving Ground, MD 21005 USA
关键词
D O I
10.1021/acs.oprd.7b00093
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A new procedure for the synthesis and isolation of methyl nitroacetate is described. The previously published method required drying the explosive dipotassium salt of nitroacetic acid in a vacuum desiccator, followed by grinding this material into a fine powder with a mortar and pestle prior to esterification. To obtain the desired product, benzene was employed as the extraction solvent, sodium sulfate was used as the drying agent, and two distillations were required. The new procedure eliminates drying and grinding of the explosive dipotassium salt, employs ethyl acetate or dichloromethane as the extraction solvent, eliminates the need for a drying agent, and requires a single distillation to furnish the end product in high yield and purity.
引用
收藏
页码:1088 / 1090
页数:3
相关论文
共 50 条
  • [1] Safer, greener route to methyl nitroacetate
    Halford, Bethany
    CHEMICAL & ENGINEERING NEWS, 2017, 95 (26) : 8 - 8
  • [2] METHYL NITROACETATE
    ZEN, S
    KOYAMA, M
    KOTO, S
    ORGANIC SYNTHESES, 1988, 50-9 : 797 - 799
  • [3] Methyl nitroacetate and 3-nitropropionate in the synthesis of hexahydropyrimidines and piperidines
    Shakirov, R. R.
    Dokichev, T. V.
    Biglova, R. Z.
    Vlasova, N. M.
    Baibulatova, N. Z.
    Talipov, R. F.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (01) : 43 - 49
  • [4] Methyl nitroacetate and 3-nitropropionate in the synthesis of hexahydropyrimidines and piperidines
    R. R. Shakirov
    T. V. Dokichev
    R. Z. Biglova
    N. M. Vlasova
    N. Z. Baibulatova
    R. F. Talipov
    Chemistry of Heterocyclic Compounds, 2008, 44 : 43 - 49
  • [5] A Convenient Synthesis of (-)-Methyl Epijasmonate
    U, J. S.
    Park, H. S.
    Gupta, S.
    Cha, J. K.
    Synthetic Communications, 27 (17):
  • [6] A convenient synthesis of (-)-methyl epijasmonate
    Sun, J
    Park, HS
    Gupta, S
    Cha, JK
    SYNTHETIC COMMUNICATIONS, 1997, 27 (17) : 2931 - 2941
  • [7] Acylation of aliphatic diamines with methyl nitroacetate
    Lyapkalo, IM
    Ioffe, SL
    Strelenko, YA
    Tartakovsky, VA
    RUSSIAN CHEMICAL BULLETIN, 1996, 45 (09) : 2245 - 2247
  • [8] The Applications of Microwave Irradiation as Greener and Convenient Procedure in Organic Synthesis
    Liu, Ming
    Kong, Bo
    He, Fengdan
    Hu, Wenxiang
    2010 THE SECOND CHINA ENERGY SCIENTIST FORUM, VOL 1-3, 2010, : 94 - 97
  • [9] A convenient synthesis of γ-methyl α-(alkylidene)-γ-butyrolactones
    Shet, JB
    Amonkar, CP
    Nadkarni, VS
    Tilve, SG
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2005, 44 (07): : 1505 - 1508
  • [10] CONVENIENT SYNTHESIS OF METHYL METHYLTHIOMETHYL SULFOXIDE
    OGURA, K
    TSUCHIHA.G
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (07) : 2203 - +