A Visual Organic Chemistry Reaction: The Synthesis of 4-Amino-3-nitrobenzoic Acid Methyl Ester via Fischer Esterification

被引:4
|
作者
Kam, Caleb M. T. [1 ]
Levonis, Stephan M. [1 ]
Schweiker, Stephanie S. [1 ]
机构
[1] Bond Univ, Fac Hlth Sci & Med, Med Chem Grp, Robina, Qld 4229, Australia
关键词
Esters; Synthesis; Second-Year Undergraduate; Organic Chemistry; Hands-On Learning/Manipulatives;
D O I
10.1021/acs.jchemed.9b01168
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of 4-amino-3-nitrobenzoic acid methyl ester is a simple Fischer esterification reaction designed as an experiment for use in an introductory organic chemistry course. The compound was synthesized as a one-pot reaction within 30 min to 16 h, with 1 h producing a workable yield. The bright-yellow solid was purified using liquid-liquid extraction, and the extraction process was monitored by a marked color change. The product was then characterized by H-1 and C-13 NMR spectroscopy and thin-layer chromatography.
引用
收藏
页码:1997 / 2000
页数:4
相关论文
共 50 条
  • [1] Effect of 4-amino-3-nitrobenzoic acid on the expression level of the trans-sialidase gene in Trypanosoma cruzi epimastigotes
    Vazquez-Jimenez, Lend K.
    Paz-Gonzalez, Alma D.
    Kashif, Muhammad
    Juarez-Rendon, Karma J.
    Nogueda-Torres, Benjamin
    Bocanegra-Garcia, Virgilio
    Rivera, Gildardo
    [J]. PAKISTAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2019, 32 (02) : 825 - 829
  • [2] Total synthesis of (±)-epithuriferic acid methyl ester via Diels-Alder reaction
    Koprowski, Marek
    Balczewski, Piotr
    Owsianik, Krzysztof
    Rozycka-Sokolowska, Ewa
    Marciniak, Bernard
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (05) : 1822 - 1830
  • [3] A short synthesis of azasugars via aldol reaction of chelated amino acid ester enolates
    Grandel, R
    Kazmaier, U
    [J]. TETRAHEDRON LETTERS, 1997, 38 (46) : 8009 - 8012
  • [4] Chromium-tungsten-manganese oxides for synthesis of fatty acid methyl ester via esterification of palm fatty acid distillate
    Wan, Zuraida
    Lim, J. K.
    Hameed, B. H.
    [J]. ENERGY, 2017, 141 : 1989 - 1997
  • [5] Aziridinium ions in organic synthesis:: β-amino ester formation via the aziridinium carbonylation reaction.
    Burns, EE
    Brannon, JK
    Kaufman, M
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U104 - U104
  • [6] Transmutation of Scent: An Evaluation of the Synthesis of Methyl Cinnamate, a Commercial Fragrance, via a Fischer Esterification for the Second-Year Organic Laboratory
    Steele, Jacob H.
    Bozor, Marie X.
    Boyce, Gregory R.
    [J]. JOURNAL OF CHEMICAL EDUCATION, 2020, 97 (11) : 4127 - 4132
  • [7] Green organic chemistry experiments: Glyoxylamide synthesis via ring opening of N-acetylisatins with amino acid methyl esters
    Xu, Lin
    Yin, Qin
    Desrochers, Linda
    Goodwin, Thomas
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [8] Transforming honey into strawberries: The Fischer esterification of cinnamic acid to methyl cinnamate as an engaging experiment for the second-year organic chemistry laboratory.
    Boyce, Gregory
    Steele, Jacob
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [9] Improved Synthesis of 3,3-Dimethyl-4-Pentenoic Acid Methyl Ester
    Liao, Yan-fang
    Yu, Hui-qun
    Mo, You-bin
    Zhou, Hai
    Peng, Chu-he
    [J]. PROGRESS IN MATERIALS AND PROCESSES, PTS 1-3, 2013, 602-604 : 1269 - 1273
  • [10] Solubility of 4-methyl-3-nitrobenzoic acid in organic mono-solvents: calculation of Abraham model solute descriptors
    Wang, Shang
    Liu, Kelly
    Zhang, Alex
    Dai, Jingyi
    Gupta, Avi
    Zhu, Siqi
    Eddula, Shrika
    Jiang, Carina
    Acree, William E., Jr.
    Abraham, Michael H.
    [J]. PHYSICS AND CHEMISTRY OF LIQUIDS, 2020, 58 (06) : 782 - 791