Citation: Yanji Huang, Binyang Liu, Min Yu, Min Lin, Jinmei Zhou, Lirong Lin. Improvement and Extensive Design of the Synthesis of Coumarin-3-carboxylic Acid[J]. University Chemistry, ;2023, 38(2): 214-220. doi: 10.3866/PKU.DXHX202205061 shu

Improvement and Extensive Design of the Synthesis of Coumarin-3-carboxylic Acid

Yanji Huang ¹ ,
Binyang Liu ¹ ,
Min Yu ¹ ,
Min Lin ² ,
Jinmei Zhou ² ,
Lirong Lin ¹

1.
College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian Province, China;
2.
National Demonstration Center for Experimental Chemistry Education, Xiamen University, Xiamen 361005, Fujian Province, China

Received Date: 18 May 2022

The preparation of coumarin-3-carboxylic acid is a classical chemistry experiment. In this experiment, the reactants, salicylaldehyde and diethyl malonate, as well as the piperidine catalyst are mixed under reflux for 2 h to obtain coumarin-3-carboxylic acid after base hydrolysis and acidification. We have made the following improvements and extensive designs to the experiment: 1) By substituting diethyl malonate with Meldrum’s acid, coumarin-3-carboxylic acid can be obtained by heating at 90 °C for 30 min in water, and 7-(diethylamino)coumarin-3-carboxylic acid can be synthesized by changing the substrate; 2) Observing the fluorescence of the solution with Eu³⁺, coumarin-3-carboxylic acid, and 7-(diethylamino)coumarin-3-carboxylic acid and using computational chemistry can help verify the energy transfer property. The modified experiment, which involves a number of important multidisciplinary knowledge points, has strong modularity, comprehensiveness, interest, and teaching feasibility. Moreover, it is conducive to cultivating students’ innovative and comprehensive application abilities.
- Coumarin-3-carboxylic acid,
- Knoevenagel condensation reaction,
- Fluorescence,
- Energy transfer
1. [1]
  Stefanachi, A.; Leonetti, F.; Pisani, L.; Catto, M.; Carotti, A. Molecules 2018, 23 (2), 250.
2. [2]
  Cao, D.; Liu, Z.; Verwilst, P.; Koo, S.; Jangjili, P.; Kim, J. S.; Lin, W. Chem. Rev. 2019, 119 (18), 10403.
3. [3]
  Carla, F.; Cristina, F.; André, C.; Álvaro, N.; Valdemar, L. Curr. Org. Chem. 2019, 23 (24), 2722.
4. [4]
5. [5]
6. [6]
7. [7]
8. [8]
9. [9]
  Maggi, R.; Bigi, F.; Carloni, S.; Mazzacani, A.; Sartori, G. Green Chem. 2001, 3 (4), 173.
10. [10]
  Deshmukh, M. N.; Burud, R.; Baldino, C.; Chan, P. C. M.; Liu, J. F. Syn. Commun. 2003, 33 (19), 3299.
11. [11]
12. [12]
  Chavan, H.; Bandgar, B. ACS Sustainable Chem. Eng. 2013, 1 (8), 929.
13. [13]
  Pihlaja, K.; Seilo, M. Acta Chem. Scand. 1969, 23 (9), 3003.
14. [14]
  Sato, S.; Wada, M. Bull. Chem. Soc. Jpn. 1970, 43 (7), 1955.
1. [1]
  Qi Wu , Changhua Wang , Yingying Li , Xintong Zhang . Enhanced photocatalytic synthesis of H₂O₂ by triplet electron transfer at g-C₃N₄@BN van der Waals heterojunction interface. Acta Physico-Chimica Sinica, 2025, 41(9): 100107-0. doi: 10.1016/j.actphy.2025.100107
2. [2]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
3. [3]
  Feng Lu , Tao Wang , Qi Wang . Preparation and Characterization of Water-Soluble Silver Nanoclusters: A New Design and Teaching Practice in Materials Chemistry Experiment. University Chemistry, 2025, 40(4): 375-381. doi: 10.12461/PKU.DXHX202406005
4. [4]
  Hao YAN , Meng WANG , Chenyi HU , Ming LI , Chuanjun YUAN . Synthesis of europium complex bonded NaYF₄∶Yb, Er micron-materials and their applications in dual-mode fluorescent development of latent fingerprints. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 991-1002. doi: 10.11862/CJIC.20250302
5. [5]
  YanYuan Jia , Rong Rong , Jie Liu , Jing Guo , GuoYu Jiang , Shuo Guo . Unity is Strength, and Independence Shines: A Science Popularization Experiment on AIE and ACQ Effects. University Chemistry, 2024, 39(9): 349-358. doi: 10.12461/PKU.DXHX202402035
6. [6]
  Qin Li , Kexin Yang , Qinglin Yang , Xiangjin Zhu , Xiaole Han , Tao Huang . Illuminating Chlorophyll: Innovative Chemistry Popularization Experiment. University Chemistry, 2024, 39(9): 359-368. doi: 10.3866/PKU.DXHX202309059
7. [7]
  Zehua Zhang , Haitao Yu , Yanyu Qi . Design Strategy for Thermally Activated Delayed Fluorescence Materials with Multiple Resonance Effect. Acta Physico-Chimica Sinica, 2025, 41(1): 100006-0. doi: 10.3866/PKU.WHXB202309042
8. [8]
  Wenwei Zeng , Qingyu Sun , Mengxiang Liang , Lirong Lin , Laiying Zhang . Unveiling Anti-Counterfeiting Secrets: Excitation-Dependent Luminescence in Sb³⁺-Doped Perovskite Materials. University Chemistry, 2026, 41(2): 375-384. doi: 10.12461/PKU.DXHX202503036
9. [9]
  Chen LU , Qinlong HONG , Haixia ZHANG , Jian ZHANG . Syntheses, structures, and properties of copper-iodine cluster-based boron imidazolate framework materials. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 149-154. doi: 10.11862/CJIC.20240407
10. [10]
  Yuanyu YANG , Jianhua XUE , Yujia BAI , Lulu CUI , Dongdong YANG , Qi MA . Design, synthesis, and detection of Al³⁺ of two zinc complexes based on Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1207-1216. doi: 10.11862/CJIC.20250005
11. [11]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
12. [12]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
13. [13]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
14. [14]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
15. [15]
  Jimin HOU , Mengyang LI , Chunhua GONG , Shaozhuang ZHANG , Caihong ZHAN , Hao XU , Jingli XIE . Synthesis, structures, and properties of metal-organic frameworks based on bipyridyl ligands and isophthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 549-560. doi: 10.11862/CJIC.20240348
16. [16]
  Zhenghua ZHAO , Yufeng LIU , Qing ZHANG , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of zinc(Ⅱ), nickel(Ⅱ) and cadmium(Ⅱ) complexes constructed from a terphenyl-tricarboxylate ligand. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 170-180. doi: 10.11862/CJIC.20250161
17. [17]
  Zihao XU , Lirong GUO , Jinzhong GU . Syntheses, crystal structures, and catalytic properties of zinc(Ⅱ) and cadmium(Ⅱ) coordination polymers constructed from a dicarboxylate ligand. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 1063-1072. doi: 10.11862/CJIC.20250345
18. [18]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
19. [19]
  Yan ZHAO , Xiaokang JIANG , Zhonghui LI , Jiaxu WANG , Hengwei ZHOU , Hai GUO . Preparation and fluorescence properties of Eu³⁺-doped CaLaGaO₄ red-emitting phosphors. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1861-1868. doi: 10.11862/CJIC.20240242
20. [20]
  Shuwen SUN , Gaofeng WANG . Two cadmium coordination polymers constructed by varying Ⅴ-shaped co-ligands: Syntheses, structures, and fluorescence properties. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 613-620. doi: 10.11862/CJIC.20230368

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1972)
HTML views(321)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142