Home

Citation: Qiang Feng, Siyu Wang, Qianyi Li, Xiaoyue Wang, Bing He. Air Oxidation of Benzyl Alcohol Catalyzed by Cu(I)/TEMPO System: An Comprehensive Experiment Design of Organic Chemistry[J]. University Chemistry, ;2023, 38(11): 195-205. doi: 10.3866/PKU.DXHX202304015 shu

Air Oxidation of Benzyl Alcohol Catalyzed by Cu(I)/TEMPO System: An Comprehensive Experiment Design of Organic Chemistry

Chemical Basis and Innovation Sichuan Experimental Teaching Demonstration Center, College of Chemistry and Life Sciences, Chengdu Normal University, Chengdu 611130, China

Corresponding author: Bing He, hebing@cdnu.edu.cn
Received Date: 4 April 2023

The oxidation of benzyl alcoyhol to benzaldehyde plays an important role in teaching organic chemistry. However, it is often difficult to enter basic university organic chemistry experimental teaching classes because of the unfriendly environment. In this paper, a comprehensive experiment in organic chemistry is introduced. Benzyl alcohol was efficiently oxidized to benzaldehyde in less than 30 min at room temperature using cuprous chloride, 2,2'-bipyridine (bpy), N-methylimidazole (NMI), and 2,2,6,6-tetramethylpiperidine oxide (TEMPO) as catalysts, air as oxidant, and acetone as solvent. The optimized combined catalytic system can indicate the endpoint of the reaction through color mutation; it can miniaturize the experiment, shorten the reaction time, and reduce experimental cost. Extensive experiments were conducted on benzyl alcohol compounds with different electrical properties, and the reaction exhibited wide adaptability. To some extent, this experiment compensates for the lack of experimental teaching resources for aromatic aldehyde synthesis in college chemistry teaching experiments.
- Comprehensive experiment of organic chemistry,
- Air oxidation,
- Aromatic aldehydes,
- Structural characterization
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
  Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52 (12), 2559.
6. [6]
7. [7]
  Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901.
8. [8]
  Liu, Z. Z.; Shen, Z. Q.; Zhang, N.; Zhong, W.; Li, X. M. Catal. Lett. 2018, 148 (9), 2709.
9. [9]
  Hoover, J. M.; Ryland, B. L.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 2357.
1. [1]
  Xiyuan Zhang , Rui Dong , Yang Yang , Jiapeng Ding , Zhiwei Miao . Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062
2. [2]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
3. [3]
  Fen Wang , Qi Yang , Qianfei Ye , Jichao Xiao . Synthesis of Sulfinamidines via the Oxidative Sulfonamination of Sulfenamides: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(11): 354-361. doi: 10.12461/PKU.DXHX202506059
4. [4]
  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
5. [5]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
6. [6]
  Zhenxing Liu , Jiaen Hu , Zishi Cheng , Xinqi Hao . 基础有机化学教学中烯烃的氧化反应. University Chemistry, 2025, 40(6): 139-144. doi: 10.12461/PKU.DXHX202408107
7. [7]
  Ruiying Zhao , Shuheng Luo , Jinke Li , Junjie Zhang , Min Zhu , Yang Li , Yanhong Bai , Yinhuan Li , Lijuan Wang . Ultrasonic-Assisted Synthesis of Rosacetal: A Comprehensive Research-Oriented Organic Chemistry Experiment. University Chemistry, 2025, 40(11): 300-309. doi: 10.12461/PKU.DXHX202412075
8. [8]
  Guanghui Wang , Chen Qian , Zhiyong Ma . Preparation and Characterization of 7H-Benzo[C]Carbazole Based Ultra-Long Organic Room Temperature Phosphorescence Material. University Chemistry, 2025, 40(11): 289-299. doi: 10.12461/PKU.DXHX202412062
9. [9]
  Pan Li , Huguo Shen , Cong Hua , Jinjie Fang , Xiangying Chi , Quan Jiang , Zichen Feng , Ye Kang , Bin Zheng . Synthesis and Characterization of an Aggregation-Induced Emission-Active Organic Cage Molecule: A Proposed Comprehensive Chemistry Experiment. University Chemistry, 2025, 40(11): 337-345. doi: 10.12461/PKU.DXHX202502083
10. [10]
  Zitong Chen , Zipei Su , Jiangfeng Qian . Aromatic Alkali Metal Reagents: Structures, Properties and Applications. University Chemistry, 2024, 39(8): 149-162. doi: 10.3866/PKU.DXHX202311054
11. [11]
  Guodong Xu , Chengcai Sheng , Xiaomeng Zhao , Tuojiang Zhang , Zongtang Liu , Jun Dong . Reform of Comprehensive Organic Chemistry Experiments in the Context of Emerging Engineering Education: A Case Study on the Improved Preparation of Benzocaine. University Chemistry, 2024, 39(11): 286-295. doi: 10.12461/PKU.DXHX202403094
12. [12]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
13. [13]
  Yinuo Wang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Synthesis of Bromobenzoxazine: Introduce a Comprehensive Organic Chemistry Experiment Transformed from Undergraduate Research Innovation. University Chemistry, 2025, 40(10): 208-216. doi: 10.12461/PKU.DXHX202411077
14. [14]
  Gang Liu , Heng Zhang , Ying Ma , Shiling Yuan , Qisheng Song , Zhenghu Xu , Jichao Sun . Exploration and Practice on Improving the Teaching Quality of Organic Chemistry Laboratory Course. University Chemistry, 2024, 39(4): 70-74. doi: 10.3866/PKU.DXHX202309079
15. [15]
  Houjin Li , Wenjian Lan . Name Reactions in University Organic Chemistry Laboratory. University Chemistry, 2024, 39(4): 268-279. doi: 10.3866/PKU.DXHX202310016
16. [16]
  Houjin Li , Shuanglian Cai , Yuan Zheng , Zhanxiang Liu , Chengshan Yuan , Lin Wu , Guangao Yu , Jie Han , Qingwen Liu , Xin Du , Ying Xiong , Qihan Zhang , Xingwen Sun , Jianrong Zhang , Shuyong Zhang . Basic Operations and Standardization Suggestions for Organic Chemistry Distillation Experiments. University Chemistry, 2025, 40(5): 40-54. doi: 10.12461/PKU.DXHX202411053
17. [17]
  Zhanxiang Liu , Chengshan Yuan , Jie Han , Shuanglian Cai , Qihan Zhang , Lin Wu , Yuan Zheng , Xingwen Sun , Qingwen Liu , Ying Xiong , Guangao Yu , Xin Du , Houjin Li , Jianrong Zhang , Shuyong Zhang . Recommendations for Basic Operations and Standards for Organic Chemical Extraction and Washing Experiments. University Chemistry, 2025, 40(5): 55-65. doi: 10.12461/PKU.DXHX202410039
18. [18]
  Xuewei Qian , Xingwen Sun , Houjin Li , Zhanxiang Liu , Yuan Zheng , Lin Wu , Shuanglian Cai , Ying Xiong , Guangao Yu , Qingwen Liu , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Shuyong Zhang , Jianrong Zhang . Basic Operations and Specification Suggestions for Organic Chemical Recrystallization Experiments. University Chemistry, 2025, 40(5): 66-75. doi: 10.12461/PKU.DXHX202503126
19. [19]
  Chengshan Yuan , Zhanxiang Liu , Xin Du , Jie Han , Yuan Zheng , Ying Xiong , Qingwen Liu , Guangao Yu , Lin Wu , Shuanglian Cai , Xingwen Sun , Qihan Zhang , Houjin Li , Jianrong Zhang , Shuyong Zhang . Standardized Operational Guidelines for Sublimation in Organic Chemistry Experiments. University Chemistry, 2025, 40(5): 76-83. doi: 10.12461/PKU.DXHX202504015
20. [20]
  Yuan Zheng , Houjin Li , Zhanxiang Liu , Lin Wu , Shuanglian Cai , Ying Xiong , Guangao Yu , Xingwen Sun , Qingwen Liu , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Standardization Suggestions for Organic Chemistry Reflux Experiments. University Chemistry, 2025, 40(5): 84-92. doi: 10.12461/PKU.DXHX202411045

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(1230)
HTML views(112)

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

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return