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1 - substituted 2 - pyrrolidone and 3,5 - dimethoxybenzene formaldehyde synthetic
Author: LinFengZhen
Tutor: ZhangZhiDe
School: Shandong Normal University
Course: Organic Chemistry
Keywords: pyrrolidinone aromatic amine alicyclic amine aliphatic amine phosphoric acid 3,5-dimethoxybenzaldehyde 4-aminotoluene acid-hydrolyzation
CLC: TQ25
Type: Master's thesis
Year: 2005
Downloads: 188
Quote: 0
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Abstract
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This dissertation consists of two parts: Part One: The preparation of series of 1-substituted-2-pyrrolidinones from γ-butyrolactone and aromatic amine, alicyclic amine, aliphatic amine has been discussed. The compounds of 1-substituted-2-pyrrolidinones are a kind of important synthetic intermediate. They are used widely in the industry of fine chemicals. Firstly, in this dissertation,1-phenyl-2-pyrrolidinone(NPP) was prep-ared by γ-butyrolactone and aniline catalyzed by phosphoric acid. Factors influencing the reaction were studied and the optimum process conditions were determined. This experiment is catalyzed by phosphoric acid. Aniline was recovered by distillation and separated from water, and the residue as catalyst was reused. NPP was separated through reductive distillation directly and recrystallized to purification. This method increased the yield and purity. The technics simplified the reaction and reduced the cost. The raw material and catalyst were reused. In this technic condition, we studied the reaction between more aromatic amine and γ-butyrolactone. Through the yield of the products, we compared the reactivity of different aromatic amines and researched the influence of the electron effection and space effection to the reaction. Based on the reaction between aromatic amines and γ-butyrolactone, we studied the reaction between γ-butyrolactone and alicyclic amine or aliphatic amine. The preparation of 1-cyclohexyl-2-pyrrolidinone (CHP) is the same as the preparation of 1-aryl-2-pyrrolidinone. 1-Cyclohexyl-2-pyrrolidinone was prepared from cyclohexylamine and γ-butyrolactone catalyzed by phosphoric acid. Cyclohexylamine was recovered by distillation and separated from water. CHP was obtained through reductive distillation directly. But the preparation of 1-alkyl-2-pyrro-lidinone was different from 1-aryl-2-pyrrolidinone. It need stepwise-synthesis. Firstly,aliphatic amine and γ-butyrolactone reacted to produce hydroxyamide. Then, hydroxyzmide formated 1-alkyl-2-pyrrolidinone through cyclodehydration. We discussed the influence of the reactive conditions and studied the preparation of 1-alkyl-2-pyrrolidinone and nine aliphatic amines. The products were certified by melting point, IR, 1HNMR and elementary analysis. Part Two: We studied new preparative technics of 3,5-dimethoxybenzaldehyde (DMB).we discussed the reaction to prepare the series of 3,5-dimethoxybenzaldehyde through different reactive path. We put more emphasis on the route which is from 4-aminotoluene. 3,5-dimethoxybenzaldehyde is a very important intermediate and are used widely in the preparation of medicament. DMB is a new material intermediate. On the base of DMB, we can transform it into
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