Method for preparing 5-nitro vanillin

A technology of nitrovanillin and vanillin, applied in the field of preparation of 5-nitrovanillin, which can solve the problems of complex product separation process, large amount of waste acid waste water, increased side reactions, etc., and shorten the reaction time , low production cost and easy operation

Inactive Publication Date: 2012-01-04
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method uses a large amount of acid and a large amount of waste acid waste water, which is not conducive to environmental protection.
At the same time, due to the strong oxidizing properties of nitric acid, side reactions are also increased, and the product separation process is complicated.

Method used

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  • Method for preparing 5-nitro vanillin
  • Method for preparing 5-nitro vanillin
  • Method for preparing 5-nitro vanillin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] In a 25mL Erlenmeyer flask, add 0.152g (1mmol) vanillin, 2mL volume fraction 90% acetic acid, 0.50g (1.25mmol) polyethylene glycol-400, slowly drop in 0.09g (0.58mmol) under stirring condition Aqueous solution of ammonium cerium nitrate, reacted at 20°C for 2.5 hours, tracked by TLC, developer: ethyl acetate: petroleum ether = 1: 1, stop stirring when the reactant is completely converted into product; pour the reactant into an appropriate amount of ice water , a yellow solid was precipitated, suction filtered, and the solid was washed 2-3 times with distilled water to obtain the crude product of 5-nitrovanillin; weighing: 0.14g, yield: 71%; the product was determined by melting point and infrared The spectrum and proton nuclear magnetic resonance spectrum analysis are consistent with the literature reports; the measured melting point is: m.p: 177.2~178.6 ℃;

[0014] IR: ν max (KBr pellets, cm -1 ), 3203, 3077, 2945, 2876, 1685, 1611, 1548, 1402, 1335, 1269, 1231, 1103...

Embodiment 2

[0016] In a 100mL Erlenmeyer flask, add 0.76g (5mmol) vanillin, 10mL volume fraction 90% acetic acid, 2.5g (6.25mmol) polyethylene glycol-400, slowly drop in 0.76g (4.9mmol) under stirring condition Aqueous solution of ammonium cerium nitrate; react at 40°C for 1.5 hours, tracked by TLC, developer: ethyl acetate: petroleum ether = 1:1, stop stirring when the reactant is completely converted into product; pour the reactant into an appropriate amount of ice water , a yellow solid was precipitated, suction filtered, and the solid was washed 2-3 times with distilled water to obtain the crude product of 5-nitrovanillin; weighing: 0.68g, yield: 69%; the measured melting point was: m.p : 177.5~178.6 ℃.

Embodiment 3

[0018] Add 15.2g (100mmol) vanillin, 200mL volume fraction 90% acetic acid, 50.0 g (125 mmol) polyethylene glycol-400 into a 1000mL round-bottomed flask, slowly drop into 24.32g (158 mmol) ) aqueous solution of ammonium cerium nitrate, reacted at 60°C for 1.0 hour, tracked by TLC, developer: ethyl acetate: petroleum ether = 1: 1, stop stirring when the reactant is completely converted into product; pour the reactant into an appropriate amount of ice In the water, a yellow solid was precipitated, filtered by suction, and washed with distilled water for 2-3 times to obtain a crude product of 5-nitrovanillin; weighing: 13.8 g, yield: 70%. The measured melting point is: m.p: 177.5~178.5 ℃.

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Abstract

The invention discloses a method for preparing 5-nitro vanillin. The method comprises the following specific steps of: dissolving vanillin and ceric ammonium nitrate in 5-90% by volume of acetic acid according to the weight ratio of the vanillin to the ceric ammonium nitrate of 1:(0.6-1.6), adding polyethylene glycol-400 as a phase transfer catalyst according to the mol ratio of the polyethylene glycol-400 to the vanillin of 1:1.25, reacting at 20-60 DEG C for 1.0-2.5 h under magnetic stirring, tracking by TLC (Thin Layer Chromatography), wherein a developing agent includes ethyl acetate and petroleum ether in the ratio of 1:1, and stopping stirring after a reactant is completely converted into a product; and pouring a mixture into proper ice water, separating out yellow solid, and obtaining the 5-nitro vanillin product by filtering, washing, drying and re-crystallizing. According to the method disclosed by the invention, the green chemical product, namely ceric ammonium nitrate, is used as a nitration reagent; the polyethylene glycol-400 is used as the phase transfer catalyst; and the method has the advantages of short reaction time, few by-products, simplicity and convenience for operation and low production cost.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of 5-nitrovanillin. Background technique [0002] 5-nitrovanillin, the systematic name is 3-methoxy-4-hydroxy-5-nitrobenzaldehyde. Mainly used in the fields of medicine and spices, it can be used in the synthesis of 3,5-disubstituted catechols catechol-O-methyltransferase (COMT-I) inhibitor tolcapone, or as a synthetic advantage Precursor for the biosynthesis of famycin antibiotics (3-hydroxymethoxyrifamycin, 3-hydroxyrifamycin). The preparation method of 5-nitrovanillin is mainly through the vanillin nitration method, that is, the vanillin is used as a raw material, and nitric acid is used as a nitrating agent to obtain it in an organic solvent. However, this method uses a large amount of acid and a large amount of waste acid waste water, which is not conducive to environmental protection. Simultaneously, because the strong oxidizing property of nitri...

Claims

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Application Information

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IPC IPC(8): C07C205/44C07C201/08
Inventor 周建峰朱惠琴娄凤文安礼涛周正权
Owner HUAIYIN TEACHERS COLLEGE
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