Aldol缩合-水解“一锅”法制备反式肉桂酸——推荐一个改进的有机合成实验

引用本文: 常煜琨, 黄昊秦, 王宝雷. Aldol缩合-水解“一锅”法制备反式肉桂酸——推荐一个改进的有机合成实验[J]. 大学化学, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095 shu

Citation: Yukun Chang, Haoqin Huang, Baolei Wang. Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment[J]. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095 shu

Aldol缩合-水解“一锅”法制备反式肉桂酸——推荐一个改进的有机合成实验

南开大学化学学院, 元素有机化学国家重点实验室, 天津 300071

通讯作者: 王宝雷, nkwbl@nankai.edu.cn

基金项目:
国家自然科学基金(22077070)

摘要: 肉桂酸是一种重要的有机合成中间体以及精细化工原料，广泛应用于多个领域。肉桂酸制备是本科生有机化学实验教学中的重要内容之一，常按照经典的以苯甲醛和乙酸酐为原料、醋酸钾/碳酸钾为催化剂的Perkin反应来进行。本文提出了一种新的方法——Aldol缩合-水解法，用于制备反式肉桂酸。该法以苯甲醛、乙酸乙酯和叔丁醇钾为原料进行反应，再以“一锅”的方式依次进行蒸馏、加碱水解、蒸馏和酸化即得反式肉桂酸纯品，具有原料/试剂廉价易得、用量少、实验装置简单、能耗小、操作便捷、产率高、耗时较短和环境污染小等优点，非常值得推荐用于本科生实验教学，更有利于对学生在掌握多方面基础理论知识和实验技能的同时，拓展便捷高效合成有机物的创新思维和提高节能环保意识等综合素质的培养。

关键词:

English

Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment

State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: Baolei Wang, nkwbl@nankai.edu.cn

Received Date: 25 September 2023
Revised Date: 29 November 2023
Available Online: 18 December 2023

Abstract: Cinnamic acid is an important intermediate in organic synthesis and a valuable raw material in the fine chemicals industry, with a wide range of applications across various fields. The preparation of cinnamic acid is a significant component in undergraduate organic chemistry experiments. Traditionally, it is achieved through the classic Perkin reaction, using benzaldehyde and acetic anhydride as starting materials and employing potassium acetate/potassium carbonate as catalysts. This article proposes a novel approach, namely the Aldol condensation-hydrolysis method, for the synthesis of trans-cinnamic acid. In this method, benzaldehyde, ethyl acetate, and potassium tert-butoxide are used as reactants, and the reaction proceeds through a “one-pot” process involving reflux, distillation, alkali hydrolysis, distillation again, and acidification, ultimately yielding pure trans-cinnamic acid. This method offers numerous advantages, including the use of inexpensive raw materials and reagents, low quantities required, simple equipment setup, low energy consumption, easy operation, high yield, short reaction time, and minimal environmental pollution. Therefore, it is highly recommended for undergraduate experimental teaching. Furthermore, this method not only helps students acquire a comprehensive understanding of fundamental theoretical knowledge and experimental skills but also encourages them to think innovatively in terms of convenient and efficient synthesis of organic compounds. Additionally, it fosters awareness of energy conservation and environmental protection, contributing to the development of well-rounded individuals.

Key words:

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Aldol缩合-水解“一锅”法制备反式肉桂酸——推荐一个改进的有机合成实验

通讯作者: 王宝雷, nkwbl@nankai.edu.cn

English

Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment

Corresponding author: Baolei Wang, nkwbl@nankai.edu.cn

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

Aldol缩合-水解“一锅”法制备反式肉桂酸——推荐一个改进的有机合成实验

通讯作者: 王宝雷, nkwbl@nankai.edu.cn

English

Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment

Corresponding author: Baolei Wang, nkwbl@nankai.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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