Beckmann重排合成N-(2-萘基)乙酰胺的综合实验设计

doi:10.3866/PKU.DXHX202108077

Abstract

Abstract:

Beckmann rearrangement is an important experiment in field of fundamental organic chemistry laboratories for college students. Currently, refluxing the oxime solution in the presence of concentrated sulfuric acid or polyphosphoric acid is commonly used in experimental training classes. In this study, Appel's salt formed in situ by mixing triphenylphosphine and carbon tetrachloride was used to initiate the Beckmann rearrangement, which allowed the reaction to proceed at room temperature under neutral conditions. This experimental solution avoids the use of corrosive acid and high temperature; it features operational simplicity, high yield, and good repeatability, thereby providing a teaching experiment with remarkable safety advantages.

Key words: Beckmann rearrangement, Safety, Appel's salt

Nana Sun, Like Deng, Yue Sun, Weijin Gu, Bingxiang Wang, Langui Xie. Comprehensive Experiment on the Synthesis of N-2-Naphthalenylacetamide via Beckmann Rearrangement[J].University Chemistry, 2022, 37(6): 2108077.

编号	试剂	纯度	制造商
1	2-萘乙酮	≥ 98%	上海阿达玛斯试剂有限公司
2	四氯化碳	99.5%	上海阿达玛斯试剂有限公司
3	醋酸钠	分析纯	上海泰坦科技股份有限公司
4	N, N-二甲基甲酰胺	分析纯	上海泰坦科技股份有限公司
5	无水硫酸钠	分析纯	上海泰坦科技股份有限公司
6	石油醚	分析纯	上海泰坦科技股份有限公司
7	乙酸乙酯	分析纯	上海泰坦科技股份有限公司
8	无水乙醇	分析纯	上海泰坦科技股份有限公司
9	石英砂	≥ 99.0%	上海泰坦科技股份有限公司
10	三苯基膦	≥ 99.0%	上海阿拉丁生化科技股份有限公司
11	盐酸羟胺	分析纯	上海麦克林生化科技有限公司
12	硅胶	层析用	青岛鼎康硅胶公司

仪器	型号	制造商
电子分析天平	ME104T/02	METTLER TOLEDO
旋转蒸发仪	RV 3 V	德国IKA公司
双排管	M280005	北京欣维尔公司
施兰克管	25 mL	北京欣维尔公司
磁力加热搅拌器	IKA艾卡Rct Basic	德国IKA公司
核磁共振波谱仪	400 MHz	布鲁克

1	孔祥文. 有机化学实验,第2版北京:化学工业出版社,2018.
2	孙尔康;张剑荣. 有机化学实验,第3版南京:南京大学出版社,2018.
3	邱道骥;罗逾兰;马振旄;顾玮瑾;王炳祥. 南京师大学报(自然科学版),2006,29(3),50.
4	孙京国;蔡乐;刘家伟;孙晓兵;郭永岩;吴紫罗;史莹莹;冯玉玲. 化学教育(中英文),2020,41(22),62.
5	张健;刘园园;冯维春;武玉民. 有机化学,2019,39(4),961.
6	GaoP.;BaiZ. J. Chin. J. Chem.2017,35(11),1673. doi: 10.1002/cjoc.201700191
7	WeiY.;LiuY.;XieL.-G. Chin. Chem. Lett.2022,33(5),2407. doi: 10.1016/j.cclet.2021.10.020

[1]	Wenrui Yao, Ce Sun, Bailing Chen, Yuanyuan Miao, Daxin Liang, Haiyan Tan, Dingyuan Zheng, Yanhua Zhang. Practical Exploration of AI Empowerment in Graduate Safety Education [J]. University Chemistry, 2025, 40(9): 126-131.
[2]	Chen Hu, Yu Wu, Lianqing Chen, Tao Huang, Chunya Li, Lin Li, Bingguang Zhang, Peng Mei. Innovation and Exploration of Chemical Laboratory Safety Curriculum Based on the “Trinity and Four Integrations” Strategy [J]. University Chemistry, 2025, 40(8): 25-32.
[3]	Weiguang Zhao. Reflections and Recommendations on Emergency Response to Common Safety Incidents in Chemical Laboratories [J]. University Chemistry, 2025, 40(8): 291-297.
[4]	Xia Yin, Peng Yang, Feng Xu, Yan Zhao, Shuangyan Huan, Jingzhe Zhao, Gonglan Ye, Yingpeng Wu. Exploration and Practice of Ideological and Political Education in Inorganic Chemistry Experiment Course [J]. University Chemistry, 2025, 40(7): 119-126.
[5]	Wei Li, Jinfan Xu, Yongjun Zhang, Ying Guan. Preparation of Covalent Organic Framework Monolithic Material for Non-Targeted Food Safety Screening: A Recommended Comprehensive Instrumental Analysis Chemistry Experiment [J]. University Chemistry, 2025, 40(6): 276-285.
[6]	Ling Yang, Yupeng Guo, Jingcheng Ji, Xiangjuan Qi, Chuanli Qin, Pingping Zhu, Shuyong Zhang. Suggestions on Teaching Contents and Requirements of Chemistry Laboratory Safety for Chemistry Majors in Higher Education [J]. University Chemistry, 2025, 40(5): 15-22.
[7]	Jiabo Huang, Quanxin Li, Zhongyan Cao, Li Dang, Shaofei Ni. Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations [J]. University Chemistry, 2025, 40(3): 153-159.
[8]	Dan Liu, Ying Cai, Songzhi Kong. Exploration of Laboratory Safety Education Course Construction Based on "Organic Chemistry Experiment " [J]. University Chemistry, 2025, 40(10): 250-256.
[9]	Yifeng Xu, Jiquan Liu, Bin Cui, Yan Li, Gang Xie, Ying Yang. “Xiao Li’s School Adventures: The Working Principles and Safety Risks of Lithium-ion Batteries” [J]. University Chemistry, 2024, 39(9): 259-265.
[10]	Hongyan Feng, Weiwei Li. Reflections on the Safety of Chemical Science Popularization Activities [J]. University Chemistry, 2024, 39(9): 379-384.
[11]	Jiaqi Chen, Chunhui Luan, Yue Sun, Qiyun Ma, Wangfei Hao, Yanjia Wang, Xu Wu. Understanding the Dynamics of Heat and Cold through Chemistry: The Interplay of Chemical Energy and Thermal Energy [J]. University Chemistry, 2024, 39(9): 214-223.
[12]	Yongqing Kuang, Jie Liu, Jianjun Feng, Wen Yang, Shuanglian Cai, Ling Shi. Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone [J]. University Chemistry, 2024, 39(8): 331-337.
[13]	Jiaqi Chen, Shuwei Chen, Suocai Ren, Yue Sun, Chunhui Luan, Xu Wu. Exploring the People-Centered Safety Construction Model in Basic Chemistry Laboratories: A Case Study in Analytical Chemistry Laboratories [J]. University Chemistry, 2024, 39(7): 264-271.
[14]	Yong Zhou, Jia Guo, Yun Xiong, Luying He, Hui Li. Comprehensive Teaching Experiment on Electrochemical Corrosion in Galvanic Cell for Chemical Safety and Environmental Protection Course [J]. University Chemistry, 2024, 39(7): 330-336.
[15]	Anyang Li, Xiaohui Ning, Zhihui Ren, Wei Sun, Yan Li, Bin Cui. Support and Guarantee for Talent Cultivation and Discipline Development: Exploration and Practice of the Construction of National Demonstration Center for Experimental Chemistry Education in Northwest University [J]. University Chemistry, 2024, 39(7): 140-146.

Comprehensive Experiment on the Synthesis of N-2-Naphthalenylacetamide via Beckmann Rearrangement

RichHTML

PDF

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 6

References 7

Related Articles 15

Metrics

Recommended 0