由邻硝基甲苯合成邻氨基苯甲酸

武汉大学化学与分子科学学院2012级化学弘毅班有机化学设计实验

College of Chemistry and Molecular Science,

Wuhan University

Report of Organic Chemistry Experiment

Designed Experiment:Synthesis of 2-Aminobenzoic Acid

from 2-Nitrotoluene

Tutor: Ying Xiong

Student’s Name: Wenxin Lu

Major: Chemistry Class of Hongyi School

Student ID: 2012301040179

Date: Apr. 24th to May 29th, 2014(5 weeks in total, once a week)

Ⅰ. Purpose of the Experiment

1. Initiate the progress of the syntheses with the raw material, 2-nitrotoluene, to prepare the important organic synthetic raw material, 2-aminobenzoic acid, by the oxidation of potassium permanganate and the reduction of Fe/HCl.

2. Learn to use IR and 1HNMR to analysis and represent the intermediate and product, determine the purity and the structure of them.

3. Review some operations in fundamental organic chemistry experiment, such as reflux, simple distillation and recrystallization.

4. Know the common oxidation and reduction methods in organic synthesis, to strengthen the basis of theoretical study.

5. By comparing different synthesis methods, determine a simple one which has a characteristic of high yield and less pollution, to understand the idea of “Green Chemistry”.

Ⅱ. Principle of the Experiment

2-Aminobenzoic acid is an indispensable organic synthetic raw material and intermediate. In the aspect of dye, it is used to prepare anthraquinone dyes, azo dyes and indigoiddyes, in the aspect of medicine, it is used to make pontal, pyrozoline, benzydamine, tardan, etc. 2-Aminobenzoic acid is also used in organic synthesis, for example, to prepare compound like 3-hydroxyindole and methyl anthranilate. As a chemistry reagent, it is used to test cerium, cadmium, cobalt, copper, lead, magnesium, mercury, nickel, nitrite, palladium, zinc, silver and uranium.

Step 1: Oxidation of 2-Nitrotoluene

2-nitrotoluene is a derivative of arene, which has an nitryl and an adjacent methyl on benzene ring. There are some α-H atoms on the C atom directly attached to benzene ring, which can be oxidized to a carboxyl group by many kinds of oxidation.

There are various methods of preparing 2-nitrobenzoic acid from 2-nitrotoluene, and several of them are widely applied [1]:(1)Potassium permanganate method. The advantages of this method

1

相关文档