Preparation method of 3-hydroxyl phthalic anhydride

The technology of hydroxyphthalic anhydride and hydroxyphthalic acid is applied in the field of preparation of key pharmaceutical intermediate 3-hydroxyphthalic anhydride, and can solve the problems of complex process steps, high price, low yield and the like, Achieve high yield, good purity and mild conditions

Inactive Publication Date: 2017-09-01
JINAN XUANHONG BIOLOGICAL PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] Aiming at problems such as the complex process steps of the method for synthesizing 3-hydroxyphthalic anhydride in the prior art, starting materials are difficult to obtain, the price is relatively expensive, and the yield is low, the present invention proposes a 3-hydroxyphthalic anhydride preparation method

Method used

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  • Preparation method of 3-hydroxyl phthalic anhydride
  • Preparation method of 3-hydroxyl phthalic anhydride
  • Preparation method of 3-hydroxyl phthalic anhydride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add DMF100.00g, 1-methoxy-2,3-dimethylbenzene 27.24g (0.20mol) and hexadecyltrimethylammonium bromide 14.58g (0.04mol) to a 500mL three-necked flask, heat up When the temperature reaches 70°C, start to add 79.01g (0.50mol) of potassium permanganate in batches, control the temperature not to exceed 90°C, and finish adding in about 30 minutes. , filtered, washed with 100.00g of water*3 to obtain off-white solid, dried at 55-60°C, 39.23g theoretically, 30.11g actually obtained, yield 76.75%, purity 98.70%.

[0027] Add 160.01 g of dichloromethane and 30.00 g (0.15 mol) of 3-methoxyphthalic acid into a 500 mL three-necked flask, and add 76.67 g (0.31 mol) of boron tribromide dropwise in a water bath with temperature control at 10-15 ° C, dropwise After the addition was completed, the insulation reaction was continued for 6 h. Add 400.00g of ice-water mixture into another 1000mL three-neck flask, slowly pour the above reaction solution into ice water, keep the temperature n...

Embodiment 2

[0030] Add water 240.00g, 1-methoxy-2-ethyl-3-toluene 30.04g (0.20mol) and hexadecyltrimethylammonium bromide 7.29g (0.02mol) in the there-necked flask of 500mL, heat up To 80°C, start to add 63.21g (0.40mol) of potassium permanganate in batches, control the temperature not to exceed 90°C, and complete the addition in about 30 minutes. g*3 washed to obtain an off-white solid, dried at 55-60°C, theoretically 39.23g, actual obtained 32.17g, yield 82.00%, purity 98.32%.

[0031] Add 290.00 g of dichloromethane and 30.00 g (0.15 mol) of 3-methoxyphthalic acid into a 500 mL three-necked flask, and add 51.00 g (0.38 mol) of anhydrous aluminum trichloride in batches in a water bath controlled at 25-30°C. ), after adding, continue the insulation reaction for 7.5h. Add 600.00g of ice-water mixture into another 1000mL three-necked flask, slowly pour the above reaction solution into ice water, keep the temperature not exceeding 30°C, then continue stirring for 1 hour, filter, wash with ...

Embodiment 3

[0034] Add DMSO120.00g, 5-methoxy-1,2,3,4-tetrahydronaphthalene 32.45g (0.20mol) and hexadecyltrimethylammonium bromide 36.44g (0.10mol) into a 1000mL three-necked flask ), heat up to 75°C, start adding 110.62g (0.70mol) of potassium permanganate in batches, control the temperature not to exceed 90°C, finish adding in about 40 minutes, keep warm at 80-90°C for 2.5h after adding, cool down to room temperature, Add 600g of water dropwise, filter, wash with 100.00g of water*3 to obtain an off-white solid, dry at 55-60°C, theoretically 39.23g, actual 28.07g, yield 71.55%, purity 98.41%.

[0035] Add 150.00 g of 48% hydrobromic acid and 25.00 g (0.13 mol) of 3-methoxyphthalic acid into a 500 mL three-necked flask, and stir at 25-30°C for 5 h. Add 500.00g of ice-water mixture into another 1000mL three-neck flask, slowly pour the above reaction solution into ice water, keep the temperature not exceeding 30°C, then continue to stir for 1 hour, filter, wash with water until pH = 6, and...

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Abstract

The invention belongs to the technical field of organic synthesis and in particular relates to a preparation method of a key medical intermediate, 3-hydroxyl phthalic anhydride. The method comprises the following steps: with a compound I as a raw material, oxidizing the raw material to obtain 3-methoxyl phthalic acid; performing a reaction on 3-methoxyl phthalic acid to generate 3-hydroxyl phthalic acid; and performing dehydration and condensation on 3-hydroxyl phthalic acid to generate 3-hydroxyl phthalic anhydride. 3-hydroxyl phthalic anhydride prepared by the method provided by the invention is high in yield and good in purity. The method is free of special equipment demands, has mild conditions and is safe and environmental-friendly in an industrial process, and the process technology provided by the invention can be industrially performed.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of a key drug intermediate 3-hydroxyphthalic anhydride. Background technique [0002] 3-Hydroxyphthalic anhydride can be used to modify ovalbumin to prepare an active substance against herpes simplex virus in vitro, and the potential active substance drug is expected to become a new drug for preventing diseases and killing microorganisms. In addition, 3-hydroxyphthalic anhydride can be used as the modification of epoxy resin, polyester, polyimide and other heat-resistant resin raw materials. This key pharmaceutical intermediate has broad application prospects. [0003] Currently, there are usually the following synthetic methods: [0004] Method 1: 2-hydroxybutyrate ketone and acetic anhydride in concentrated sulfuric acid to generate 2-oxo-2,5-dihydrofuran, 2-oxo-2,5-dihydrofuran in triethylamine and three Methyl acetyl chloride react...

Claims

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Application Information

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IPC IPC(8): C07D307/89
CPCC07D307/89
Inventor 娄亚东李湛江
Owner JINAN XUANHONG BIOLOGICAL PHARMA CO LTD
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