Two-Step Synthesis of 4-Hydroxy-3,5-dimethylphenyl Benzoate: Undergraduate Organic Laboratory of Electrophilic Aromatic Substitution and Nucleophilic Aromatic Substitution,Journal of Chemical Education

当前位置： X-MOL 学术 › J. Chem. Educ. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Two-Step Synthesis of 4-Hydroxy-3,5-dimethylphenyl Benzoate: Undergraduate Organic Laboratory of Electrophilic Aromatic Substitution and Nucleophilic Aromatic Substitution
Journal of Chemical Education ( IF 2.5 ) Pub Date : 2024-05-15 , DOI: 10.1021/acs.jchemed.3c01270
Huifa Han ₁ , Yali Qin ₁ , Fan Wang ₁ , Ning Ding ₁ , Fang Fang ₁ , Lihong Hu ₁ , Hongming Jin ₁ , Yinan Zhang ₁

Affiliation

Electrophilic aromatic substitution (S_EAr) and nucleophilic aromatic substitution (S_NAr) reactions are among the most valuable reactions in the conversion of aromatic rings. While these reactions are typically covered in separate experiments in undergraduate organic courses, a continuous experimental setup elucidating both S_EAr and S_NAr processes remains unexplored in the literature for undergraduate laboratories. We herein described a two-step experimental design to cascade the S_EAr and S_NAr reactions, aiding students in better understanding the similarities and differences of these conversions as well as introducing the concept of umpolung. The experiment also reinforces students’ proficiency in fundamental organic synthesis techniques and workup procedures, such as TLC analysis, chromatography purification, recrystallization, and handling LRMS and NMR.

中文翻译：

4-羟基-3,5-二甲基苯基苯甲酸酯的两步合成：亲电芳香取代和亲核芳香取代本科生有机实验室

亲电芳香取代（S _E Ar）和亲核芳香取代（S _N Ar）反应是芳环转化中最有价值的反应之一。虽然这些反应通常在本科生有机课程的单独实验中进行介绍，但本科生实验室的文献中仍未探索阐明 S _E Ar 和 S _N Ar 过程的连续实验装置。我们在此描述了级联 S _E Ar 和 S _N Ar 反应的两步实验设计，帮助学生更好地理解这些转化的异同，并介绍了umpolung 的概念。该实验还增强了学生对基本有机合成技术和后处理程序的熟练程度，例如薄层色谱分析、色谱纯化、重结晶以及处理 LRMS 和 NMR。

更新日期：2024-05-15

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南