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Method for electrochemically synthesizing lactone

An electrochemical and lactone technology, applied in the direction of electrolysis process, electrolysis components, electrolysis organic production, etc., can solve the problems of unfavorable industrial operation, large-scale production, cumbersome process, etc., and achieve the effect of easy control, simple process and mild conditions

Inactive Publication Date: 2018-02-16
NANYANG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But looking at these reported C-H / O-H cross-coupling reaction lactone synthesis methods, most of them need to add transition metal catalysts, photocatalysts or organic small molecule catalysts and oxidants during the preparation process, which often requires post-processing, and the process is cumbersome , not conducive to industrial operation and mass production

Method used

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  • Method for electrochemically synthesizing lactone
  • Method for electrochemically synthesizing lactone
  • Method for electrochemically synthesizing lactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] (1) Add 40g of raw material 2-phenylbenzoic acid (1aa), 6.6g of electrolyte tetra-n-butylammonium tetrafluoroborate and 50mL of solvent acetonitrile into the non-diaphragm electrolyzer, then insert the graphite electrode with a current density of 20mA / cm 2 Constant current at 20 o Stirring reaction at C;

[0052] (2) Follow the reaction by thin-layer chromatography. After the reaction is completed, spin off the solvent under vacuum, and then isolate the lactone product by recrystallization. H -Benzo[c]chroman-6-one (2aa) 33g, yield 84%.

[0053] 1 H NMR (400 MHz, CDCl 3 ): δ 8.40-8.38 (d, J = 7.9 Hz, 1H), 8.11-8.09(d, J = 8.0 Hz, 1H), 8.05-8.03 (d, J = 7.8 Hz, 1H), 7.83-7.80 (t, J = 7.6 Hz, 1H), 7.59-7.55 (t, J = 7.6 Hz, 1H), 7.49-7.45 (t, J = 7.7 Hz, 1H), 7.36-7.31(m, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 161.1, 151.2, 134.8, 134.7, 130.5, 130.4, 128.8, 124.5, 122.7, 121.6, 121.2, 118.0, 117.7.

Embodiment 2

[0055] (1) Add 108mg of raw material 2-(4-fluorophenyl)benzoic acid (1ab), 342mg of electrolyte tetra-n-butylammonium perchlorate and 10mL of solvent acetone into the non-diaphragm electrolytic cell, and then insert the platinum electrode. Incoming current density is 10mA / cm 2 Constant current at 5 o Stirring reaction at C;

[0056] (2) Follow the reaction by thin layer chromatography. After the reaction is completed, spin off the solvent under vacuum, and then separate the lactone product 3-fluoro-6 by silica gel column chromatography. H -Benzo[c]chroman-6-one (2ab) 67mg, the yield is 63%.

[0057] 1 H NMR (400 MHz, CDCl 3 ): δ 8.38-8.36 (d, J = 7.8 Hz, 1H), 8.05-8.01(m, 2H), 7.85-7.81 (t, J = 7.6 Hz, 1H), 7.59-7.55 (t, J = 7.5 Hz, 1H), 7.09-7.06 (m, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 164.7-162.2 (d, J F-C = 249.6 Hz), 160.7, 152.2-152.1 (d, J F-C = 12.5 Hz), 135.0, 134.2, 130.6, 128.7, 124.4-124.3 (d, J F-C = 9.8 Hz), 121.5, 120.4, 114.6, 112.5-112.3 (d, J F-C = 22.2 H...

Embodiment 3

[0059] (1) Add 123mg of raw material 2-(4-methylphenyl)-4-chlorobenzoic acid (1ar), 660mg of electrolyte tetraethylammonium tetrafluoroborate and 50mL of solvent ethanol into the non-diaphragm electrolytic cell, and then insert Platinum electrode with current density of 13.3mA / cm 2 Constant current at 50 o Stirring reaction at C;

[0060] (2) Follow the reaction by thin layer chromatography. After the reaction is completed, spin off the solvent under vacuum, and then separate the lactone product 3-methyl-9-chloro-6 by silica gel column chromatography. H -Benzo[c]chroman-6-one (2ar) 55mg, the yield is 45%.

[0061] 1 H NMR (400 MHz, CDCl 3 ): δ 8.34 (d, J = 1.7 Hz, 1H), 8.02-8.00 (d, J =8.6 Hz, 1H), 7.89-7.87 (d, J = 8.5 Hz, 1H), 7.75-7.73 (dd, J = 8.6 Hz, 1.9Hz, 1H), 7.17-7.15 (d, J = 7.0 Hz, 2H), 2.45 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ160.3, 151.1, 141.8, 135.0, 134.4, 133.5, 130.0, 125.9, 123.1, 122.5, 122.2, 118.0, 114.7, 21.4.

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Abstract

The invention discloses a method for electrochemically synthesizing lactone. According to the method, carboxylic acid serves as a raw material, and electrochemical oxidation is carried out for C-H / O-Hcross coupling so as to directly obtain the lactone with various structures, such as biaryl lactone, coumarin lactone, benzofuran lactone. The synthetic method is simple in process, high in stability, green and environment-friendly and easy to control and produce in large scale, the raw materials are directly oxidized into lactone products under the electrochemical condition, and thus the methodis more efficient and rapid. In addition, the raw material substrate is wide in application range and easy to obtain, a transition metal catalyst, a photocatalyst or an organic small molecular catalyst do not need to be added in the preparation process, thus the universality of lactone synthesis is further increased, and the yield of lactone can also be improved.

Description

【Technical Field】 [0001] The invention belongs to the field of organic synthesis, and specifically relates to a method for electrochemically synthesizing lactone. 【Background technique】 [0002] As a skeleton structure, lactones are widely present in natural products or medicines. Because of their high biological activity, they have been widely used in various fields such as organic synthesis, catalytic chemistry, biomedicine, and environmental management. At present, the commonly used methods for synthesizing lactones mainly include esterification and dehydrogenation. Among them, the esterification method is formed by dehydration of hydroxy acid. Because of the need to add strong acid to catalyze the oxidation during the synthesis process, many by-products are generated, which not only pollute The environment, and the purity of the lactone is greatly reduced, and there are certain safety hazards during the use of strong acid. Although the dehydrogenation method can synthesize th...

Claims

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Application Information

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IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 张胜李丽君徐坤张旭王志强
Owner NANYANG NORMAL UNIV
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