University Chemistry ›› 2022, Vol. 37 ›› Issue (5): 2111088.doi: 10.3866/PKU.DXHX202111088

Special Issue: 第2届全国大学生化学实验创新设计竞赛

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Green Oxidative Synthesis of 2-Nitrobenzaldehyde: An Oxidative Synthesis Experiment for the Undergraduate Organic Laboratory

Sheng Li, Shuang Yang, Yonghao Liu, Zizhuo Zhao, Qi Zhang, Zhiyan Huang()   

  • Received:2021-11-30 Accepted:2021-12-07 Published:2022-04-11
  • Contact: Zhiyan Huang E-mail:zyhuang@snnu.edu.cn

Abstract:

Applying scientific-issue-oriented education, the green synthetic process of 2-nitrobenzaldehyde was modified and applied as a fundamental organic experiment for oxidation reactions in undergraduate education. Selective oxidation of 2-nitrobenzyl alcohol was achieved in the presence of 0.1 mol% water-soluble 2-(1-hydroxy-2, 2, 6, 6-tetramethylpiperidin-4-ylidene) acetic acid (TEMPO-COOH) and commercially available NaClO. The corresponding 2-nitrobenzaldehyde was obtained in 93% yield and > 99% purity. This newly designed experiment includes a series of basic organic experimentation techniques and the entire classic organic synthesis process, including reaction monitor, structure characterization, purity analysis and so on. Furthermore, the principle of green chemistry and the general way of methodology study in organic chemistry were integrated. Environmentally friendly and inexpensive starting materials, as well as the 3‒4 h experiment period, make this innovative experiment suitable for undergraduate education. Based on the experimental design, the corresponding micro-lecture concerning advances in oxidation was developed and incorporated into the education program. Thus, the collaboration of theoretical study and practical operation was achieved, improving the ability of undergraduates to solve complicated issues in organic synthesis and achieving high training quality.

Key words: Green chemistry, 2-Nitrobenzaldehyde, TEMPO-COOH, NaClO, Catalytic oxidation

MSC2000: 

  • G64