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Synthetic method of butylphthalide

A technology of apigenin A and tetrahydrofuran, which is applied in the field of chemical industry and can solve the problems such as complicated operation, many reaction steps, and difficulty in obtaining raw materials.

Inactive Publication Date: 2015-07-22
JINAN CHENGHUI SHUANGDA CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Another report uses o-bromobenzaldehyde under the action of N,N-dibutylnorephedrine to carry out alkylation reaction, then carry out formylation reaction, and then oxidize to obtain the target apigenin A. The raw material of this method is not easy to obtain , and there are many reaction steps, the operation is too cumbersome, and it is difficult to industrialize production

Method used

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  • Synthetic method of butylphthalide
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preparation example Construction

[0030] (1), Preparation of 3-butynylphthalide

[0031] Under nitrogen protection, add 100ml of tetrahydrofuran to a four-necked 500ml flask equipped with mechanical stirring, a thermometer and a drying tube, add 0.12mol of butyne sodium in 100ml of tetrahydrofuran solution (0.12mol of butyne sodium is dissolved in 100ml of tetrahydrofuran), cool down To -40°C, add dropwise 21.3 grams of 0.1mol 3-bromophthalide in 50ml tetrahydrofuran solution under stirring, control the temperature at -40--35°C and add dropwise, after the addition is complete, continue stirring for 1 hour; then use saturated saline The reaction liquid was washed, and the organic layer was separated and dried with sodium sulfate; after the desiccant was removed by filtration, the solvent tetrahydrofuran was distilled off under reduced pressure. 17.8 g of 3-butynylphthalide oil was obtained, HPLC92.7%, and purified by silica gel column chromatography to obtain 14.7 g of product, HPLC99.8%. The yield was 79%.

...

Embodiment 2

[0035] (1), Preparation of 3-butynylphthalide

[0036] Under nitrogen protection, add 100ml of tetrahydrofuran to a four-necked 500ml flask equipped with mechanical stirring, a thermometer and a drying tube, add 0.12mol of butyne sodium in 100ml of tetrahydrofuran solution (0.12mol of butyne sodium is dissolved in 100ml of tetrahydrofuran), cool down To -40°C, add dropwise 21.3 grams of 0.1mol 3-bromophthalide in 50ml tetrahydrofuran solution under stirring, control the temperature at -40--35°C and add dropwise, after the addition is complete, continue stirring for 1 hour; then use saturated saline The reaction liquid was washed, and the organic layer was separated and dried with sodium sulfate; after the desiccant was removed by filtration, the solvent tetrahydrofuran was distilled off under reduced pressure. 17.0 g of 3-butynylphthalide oil was obtained, HPLC92.3%, and purified by silica gel column chromatography to obtain 14.1 g of product, HPLC99.8%. The yield was 75.8%. ...

Embodiment 3

[0040] (1), Preparation of 3-butynylphthalide

[0041] Under nitrogen protection, equipped with mechanical stirring, a thermometer and a four-necked 1000ml flask with a drying tube, add 200ml tetrahydrofuran, add 200ml tetrahydrofuran solution of 0.24mol sodium butyne (dissolve 0.24mol sodium butyne in 200ml tetrahydrofuran), cool down To -40°C, add dropwise 42.5g of 0.2mol 3-bromophthalide in 100ml tetrahydrofuran solution under stirring, control the temperature at -40--35°C and add dropwise, after the dropwise addition is complete, continue stirring for 1 hour. Then, the reaction solution was washed with saturated brine, and the organic layer was separated and dried with sodium sulfate. After removing the desiccant by filtration, the solvent tetrahydrofuran was distilled off under reduced pressure. 35.5 g of 3-butynylphthalide oil was obtained, HPLC92.1%, and purified by silica gel column chromatography to obtain 29.2 g of product, HPLC99.83%. The yield was 78.5%.

[0042...

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Abstract

The invention belongs to technical filed of chemical engineering, and particularly relates to a synthetic method of butylphthalide. The method comprises the following steps: (1) preparation of 3-butynylphthalide, and (2) preparation of 3-butylphthalide. The step of preparation of 3-butynylphthalide comprises: in the protection of nitrogen, reacting sodium butyne with 3-bromophthalide in a tetrahydrofuran solution to obtain 3-butynylphthalide. The step of preparation of 3- butynylphthalide comprises that 3-butynylphthalide is subjected to a hydrogenation reaction in the presence of absolute ethyl alcohol and a catalyst of Pd / C to generate butylphthalide. According to the invention, the total yield can reach 70-75%, and the purity of butylphthalide can reach more than 99.5%.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a method for synthesizing apigenin A. Background technique [0002] Apigenin A is also known as 3-butylphthalide, butylphthalide, 3-butyl-1(3H)-isobenzofuranone, n-butylphthalide, CAS number 6066-49-5, molecular formula C 12 h 14 o 2 , molecular weight 190.24. [0003] Apigenin A is a component of celery volatile oil. It has strong anticonvulsant, antitumor, hypotensive and antiasthmatic pharmacological activities, and has a very broad application prospect in clinical medicine. [0004] At present, it is reported that apigenin A is prepared by reacting phthalic anhydride and Grignard reagent of bromobutane. However, this method has low yield, many side reactions, difficult purification and high risk. At the same time, it has been reported that the Grignard reagent of phthalic acid and bromobutane is used for docking. It is very clear from the art that p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/88
CPCC07D307/88Y02P20/584
Inventor 杨彦军刘战伟孟妍王素兰李跃东
Owner JINAN CHENGHUI SHUANGDA CHEM
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