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Method for synthesizing 7-hydroxy-4-methylcoumarin with solvent-free catalysis of ionic liquid

A technology of methyl coumarin and ionic liquids, applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve complex operations, high costs, and reaction conditions Harsh and other problems, to achieve the effect of simple preparation process, less corrosion, and high catalytic activity

Inactive Publication Date: 2012-01-11
GUANGDONG UNIV OF PETROCHEMICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned catalysts and catalytic technologies have problems such as high cost, harsh reaction conditions and complicated operation to varying degrees.

Method used

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  • Method for synthesizing 7-hydroxy-4-methylcoumarin with solvent-free catalysis of ionic liquid
  • Method for synthesizing 7-hydroxy-4-methylcoumarin with solvent-free catalysis of ionic liquid
  • Method for synthesizing 7-hydroxy-4-methylcoumarin with solvent-free catalysis of ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-2

[0032] Example 1-2: The effect of catalyst type on yield

[0033] Reaction conditions: Put 11.01g (0.1mol) of resorcinol and 14.32g (0.11mol) of ethyl acetoacetate into a three-necked flask. The amount of catalyst accounts for 3% (0.33g) of the amount of resorcinol. Investigate the reaction of the catalyst The results are shown in Table 1:

[0034] Table 1 The influence of the catalyst on the reaction

[0035] Serial number

[0036] The type of catalyst has a great influence on the product yield. It can be seen from Table 1 that in the absence of a catalyst, the synthesis reaction of resorcinol and ethyl acetoacetate does not occur. The catalytic efficiency of sulfamic acid is the lowest, and the catalytic activity of the N-methylpyrrolidone hydrogen sulfate ionic liquid catalyst is the highest and the yield is the highest.

Embodiment 3-7

[0037] Example 3-7: The influence of the amount of catalyst on the yield

[0038] Reaction conditions: Add 11.01g (0.1mol) of resorcinol and 13.02g (0.1mol) of ethyl acetoacetate into a three-necked flask, the reaction time is 2.5h, the catalyst is N-methylpyrrolidone hydrogensulfate, and different dosages are used to obtain The results are shown in Table 2:

[0039] Table 2 The influence of the amount of catalyst on the reaction

[0040]

[0041] Theoretically, as the amount of catalyst increases, the reaction speed increases. However, considering the reaction time and product purity, the amount of catalyst should not be too large. It can be seen from Table 2 that the amount of N-methylpyrrolidone bisulfate catalyst as a percentage of the amount of resorcinol has a certain influence on the reaction. That is, within a certain range, the yield varies with the decrease of the catalyst. When it increases and reaches the maximum value, the yield will decrease with the decrease of the ...

Embodiment 8

[0042] Embodiment 8: The best embodiment

[0043] The molar ratio of resorcinol and ethyl acetoacetate is 1:1.1, the catalyst is N-methylpyrrolidone hydrogen sulfate, the amount is 3% of the amount of resorcinol, and the reaction reflux time is 2.5h. The yield obtained under this improved synthesis process can reach 69.60%.

[0044] a. The product structure identification and analysis of Example 8 was carried out by infrared spectrum analysis method, and the specific analysis conditions were:

[0045] Instrument: Shimadzu Fourier Transform Infrared Spectrometer IRAffinity-1; Carrier: KBr

[0046] FT-IRumax of the product: (KBr) cm: 3157cm -1 (Ar-H), 1677cm -1 (C=O), 1608cm -1 , 1450cm -1 Is the skeleton vibration of the benzene ring, 1388cm -1 (CH 3 ), 1068cm -1 (C-O), 844cm -1 Corresponding to the C=O-H out-of-plane bending vibration outside the benzene ring, (such as figure 1 Shown).

[0047] Melting point: The synthetic 7-hydroxy-4-methylcoumarin has a melting point of 188℃-192℃.

[...

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Abstract

The invention relates to a synthetic method of a heterocyclic compound, and concretely relates to a method for synthesizing 7-hydroxy-4-methylcoumarin with the solvent-free catalysis of an ionic liquid. The method essentially comprises that resorcinol and ethyl acetoacetate are subjected to an ester interchange reaction under the effect of a catalyst, wherein the catalyst is an ionic liquid catalyst which is N-methylimidazolium hydrogensulfate or N-methylpyrrolidinone hydrogensulfate. The ionic liquid catalyst of the present invention has the advantages of simple preparation technology, easy separation from products, recovery and utilization, less corrosion to equipment, high catalytic activity, high yield, and high purity of the preparative products.

Description

Technical field [0001] The invention relates to a method for synthesizing heterocyclic compounds, in particular to a method for ionic liquid to catalyze the synthesis of 7-hydroxy-4-methylcoumarin without solvent. Background technique [0002] The chemical name of Coumarin is benzoα-pyrone. It is an important heterocyclic compound. Coumarin compounds have obvious physiological and biological activities, such as anticoagulant, antibacterial and anticancer. It is also optically active and can be used to produce fluorescent whitening agents, fluorescent disperse dyes and laser dyes. In addition, coumarin compounds are also widely used in the production of spices, pesticides, foods and cosmetics. Therefore, the synthesis of coumarin compounds has always been a research hotspot in the field of organic synthesis and pharmacy. [0003] 7-Hydroxy-4-methylcoumarin is an important coumarin compound and an important intermediate for the synthesis of fragrances, cosmetics, medicines, pestici...

Claims

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Application Information

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IPC IPC(8): C07D311/16B01J31/02
Inventor 滕俊江乔艳辉李春海
Owner GUANGDONG UNIV OF PETROCHEMICAL TECH
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