Preparation method of butylphthalide

A technology of apigenin A and phthalic anhydride, applied in the direction of organic chemistry, can solve the problems of unavailable raw materials, many reaction steps, cumbersome operation, etc., and achieve the effect of easy industrial production, few reaction steps, and simple process operation

Inactive Publication Date: 2011-02-02
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The raw materials of this method are not easy to obtain, and there are many reac

Method used

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  • Preparation method of butylphthalide
  • Preparation method of butylphthalide

Examples

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Embodiment 1

[0020] (1), Preparation of Bromobutane Grignard Reagent

[0021] Under the protection of nitrogen, add 200ml of tetrahydrofuran, 6g of magnesium flakes and 0.1g of iodine into a 500ml four-neck flask equipped with electromagnetic stirring, a thermometer and a reflux condenser with a drying tube. 31.5g of bromobutane, control the temperature not to exceed 70°C, after the dropwise addition, continue to stir for 1h to obtain the Grignard reagent of bromobutane;

[0022] (2), preparation of o-valerylbenzoic acid

[0023] Under the protection of nitrogen, add 300ml of tetrahydrofuran, 30g of phthalic anhydride and 2.5g of copper iodide into a 1L four-neck flask, cool to -20°C, add the above-mentioned Grignard reagent of bromobutane dropwise, and the dropwise addition time After the dropwise addition, continue to stir for 2 hours, add 1mol / L hydrochloric acid solution to hydrolyze to pH 2, let stand to separate the water layer, extract the water layer twice with methyl tert-butyl e...

Embodiment 2

[0027] (1) Preparation of Chlorobutane Grignard Reagent

[0028] Under the protection of nitrogen, add 200ml of tetrahydrofuran, 6g of magnesium flakes and 0.1g of iodine into a 500ml four-neck flask equipped with electromagnetic stirring, a thermometer and a reflux condenser with a drying tube. 21.3g chlorobutane, the temperature is controlled not to exceed 70°C. After the dropwise addition, continue to stir for 1h to obtain the Grignard reagent of chlorobutane;

[0029] (2), preparation of o-valerylbenzoic acid

[0030] Under the protection of nitrogen, add 300ml of tetrahydrofuran, 30g of phthalic anhydride and 2.5g of copper iodide into a 1L four-neck flask, cool to -20°C, add the above-mentioned Grignard reagent of chlorobutane dropwise, and the dropwise addition time After the dropwise addition, continue to stir for 2 hours, add 1mol / L hydrochloric acid solution to hydrolyze to pH 2, let stand to separate the water layer, extract the water layer twice with methyl tert-...

Embodiment 3

[0034] (1), Preparation of Bromobutane Grignard Reagent

[0035] Under the protection of nitrogen, add 200ml of tetrahydrofuran, 6g of magnesium flakes and 0.1g of iodine into a 500ml four-neck flask equipped with electromagnetic stirring, a thermometer and a reflux condenser with a drying tube. 31.5g of bromobutane, the temperature is controlled not to exceed 70°C, after the dropwise addition is completed, continue to stir for 1 hour to obtain the Grignard reagent of bromobutane;

[0036] (2), preparation of o-valerylbenzoic acid

[0037] Under the protection of nitrogen, add 300ml of tetrahydrofuran, 30g of phthalic anhydride and 2.5g of copper bromide into a 1L four-neck flask, cool to -20°C, add the above-mentioned Grignard reagent of bromobutane dropwise, and add the time After the dropwise addition, continue to stir for 2 hours, add 1mol / L hydrochloric acid solution to hydrolyze to pH 2, let stand to separate the water layer, extract the water layer twice with methyl te...

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Abstract

The invention discloses a preparation method of butylphthalide, which comprises the following steps: taking phthalic anhydride as a raw material; enabling the phthalic anhydride to carry out addition reaction with the Grignard reagent of butyl halide to obtain an intermediate of o-valeryl benzoic acid; and then, reducing by sodium borohydride, and carrying out acidic cyclization to obtain the butylphthalide. The phthalic anhydride and the butyl halide which are used as raw materials in the preparation method of the butylphthalide of the invention are commercial products, and the reaction raw materials can be obtained easily. Because the Grignard reaction, the sodium borohydride reduction and the acidic cyclization are classical reactions, the operation is simple, the industrialized production can be realized easily, the yield of the butylphthalide reaches 50-60%, and the purity of the butylphthalide reaches 97-98%.

Description

technical field [0001] The invention relates to a preparation method of apigenin A. Background technique [0002] Apigenin A is the main component of celery volatile oil, and it also widely exists in other plants. Apigenin has strong anti-convulsant, anti-asthma, inhibits prostaglandin F 2X , increase blood flow, anti-tumor and antihypertensive and other pharmacological activities, indicating that it has broad application prospects in clinical medicine. [0003] Nakia, R et al. reported that apigenin A was prepared by the Grignard reaction of phthalic acid and bromobutane. Although this method is simple to operate and the raw materials are readily available, the yield is low. Li Shaobai et al. reported that phthalic anhydride and valeric anhydride were used to obtain 3-butenylphthalide under the action of anhydrous sodium acetate, and then apigenin was obtained by Pd / C hydrogenation reduction. The operating conditions of this method are harsh, and the yield is also low. ...

Claims

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Application Information

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IPC IPC(8): C07D307/88
Inventor 王之建梁立冬赵延伟贾卫民
Owner SHANGHAI INST OF TECH
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