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A kind of preparation method of 2-carbonyl furan compounds

A carbonylfuran and compound technology, which is applied in the field of preparation of 2-carbonylfuran compounds, can solve the problems of not being able to realize environmental protection and high yield at the same time, and achieve considerable economic effects, important social significance, and easy-to-handle effects

Active Publication Date: 2017-12-05
JIANGSU QINGQUAN CHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to overcome the defect that the preparation method of a 2-carbonylfuran compound in the prior art cannot realize environmental protection and high yield at the same time, and provide a new green and efficient preparation method of 2-carbonylfuran compound

Method used

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  • A kind of preparation method of 2-carbonyl furan compounds
  • A kind of preparation method of 2-carbonyl furan compounds
  • A kind of preparation method of 2-carbonyl furan compounds

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preparation example Construction

[0016] The present invention provides a kind of preparation method of the 2-carbonylfuran compound of structure shown in formula (I), and this method comprises the following steps:

[0017] (1) In the presence of an acidic catalyst, the furan compound of the structure shown in the formula (II) and the general formula R 1 The aldehyde compound of CHO undergoes condensation reaction;

[0018] (2) Under the condition of oxidation reaction, carry out oxidation reaction with the condensation product of step (1) and oxidizing agent;

[0019] Formula (I), Formula (II),

[0020] R 1 In CHO and general formula (I), R 1 It is an alkyl group with 1-5 carbon atoms, carboxyl group, an alkyl carboxyl group with 2-6 carbon atoms, or an aldehyde group with 1-5 carbon atoms;

[0021] In formula (I) and formula (II), X is H, an alkyl group with 1-5 carbon atoms, an alkoxy group with 1-5 carbon atoms, acetyl, propionyl, butyryl, pentanoyl, Halogen, hydroxyalkyl group with 1-5 carbon ato...

Embodiment approach

[0039] According to one embodiment, when a solid acid catalyst is used, it is necessary to remove the solids after mixing with the neutralizing agent, which may be a conventional option in the art. For example, it can be removed by filtration. The removal method of the solvent in the neutralized mixture may be conventionally selected in the art, for example, it may be by distillation under reduced pressure.

[0040] According to the present invention, the oxidant used in step (2) can be a conventional selection in the art, for example, the oxidant can be selected from air, oxygen, hydrogen peroxide, TBHP (tert-butyl hydroperoxide), TEMPO (2,2 ,6,6-tetramethylpiperidine-nitrogen-oxide), TEMPO / TiO 2 , PCC (pyridinium chlorochromate), PDC (pyridinium dichromate), SeO 2 , CrO 3 and at least one of potassium permanganate. Preferably, the oxidizing agent is selected from TEMPO, TEMPO / TiO 2 , at least one of oxygen and TBHP.

[0041] In the present invention, the furan compound...

Embodiment 1

[0051] This example is used to illustrate the preparation method of the 2-carbonylfuran compound provided by the present invention.

[0052] Weigh 6.8g of furan and 0.55g of sulfuric acid / diatomaceous earth in a 250ml reaction flask, add 20g of acetonitrile, preheat to 15°C and keep warm for 0.5h, and slowly add 7.4g of glyoxylic acid aqueous solution with a concentration of 40% by weight dropwise to The reaction bottle was stirred vigorously, and after 10 minutes of dropwise addition, the reaction was carried out at 0°C for 5 hours. Based on glyoxylic acid, the conversion rate of furan was 75.6%, and the selectivity of 2-hydroxy-2-furan acetic acid was 84.6%.

[0053] The resulting reaction solution was neutralized and filtered to remove solids, and the low boilers were removed by distillation under reduced pressure, and 20 g of water and 0.5 g of TEMPO / TiO were added. 2 At 40°C, 80ml of hydrogen peroxide with a concentration of 27% by weight was slowly added dropwise to the...

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Abstract

The invention relates to the field of synthesis of carbonylfuran compounds and discloses a preparation method of the 2-carbonylfuran compounds adopting a structure shown in a formula (I). The method comprises the following steps: (1) a furan compound adopting a structure shown in a formula (II) and an aldehyde compound with the general formula of R1CHO have a condensation reaction in presence of an acid catalyst; (2) a condensation product in the step (1) and an oxidizing agent have an oxidation reaction under conditions of the oxidation reaction. Compared with the traditional method taking furan as the raw material and adopting acetylation and sodium nitrite oxidation technologies, the preparation method of the 2-carbonylfuran compounds has the advantages that few salts are contained in wastewater, the treatment is easy, the reaction technologies are clean and environment-friendly, and the yield is higher.

Description

technical field [0001] The invention relates to the field of synthesis of carbonyl furan compounds, in particular to a preparation method of 2-carbonyl furan compounds. Background technique [0002] 2-Carbonyl furan compounds are a class of important pharmaceutical and spice intermediates, among which 2-oxo-2-furan acetic acid is an important intermediate of cefuroxime. [0003] CN102010390A discloses a synthetic method of 2-oxo-2-furan acetic acid. The method starts from furoic acid and obtains 2-acetylformyl chloride by chlorination with thionyl chloride, and then cyanides it with sodium cyanide or potassium cyanide. , and finally hydrolyzed under acidic conditions to obtain the product. However, this method has the disadvantages of low reaction product yield, sticky product and difficult separation. [0004] CN101538255A discloses a method for synthesizing 2-oxo-2-furan acetic acid. The method uses acetylfuran as a raw material, and under acidic conditions, uses nitrate...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/46
CPCC07D307/46
Inventor 聂振中赖玉龙黄优优李伟周龙飞郭燕娜
Owner JIANGSU QINGQUAN CHEM CO LTD
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