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Method for preparing 2-iodoxybenzoic acid

A technology of iodoyl benzoic acid and iodobenzoic acid, applied in directions such as organic chemistry, can solve the problems of unstable performance, low catalytic activity, poor safety and the like

Inactive Publication Date: 2019-02-01
ZHEJIANG GUOBANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Aiming at the defects such as low catalytic activity, unstable performance, and poor safety in the existing IBX synthesis, this application provides a method for preparing 2-iodylbenzoic acid with low toxicity, mild process conditions, low cost and suitable for industrial production

Method used

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  • Method for preparing 2-iodoxybenzoic acid
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  • Method for preparing 2-iodoxybenzoic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: Synthesis of 2-iodobenzoic acid (IBX)

[0020] In the present embodiment, the principle of synthesizing 2-iodoylbenzoic acid is shown in the following formula:

[0021]

[0022] Concrete reaction condition is as follows:

[0023] Add 2-iodobenzoic acid (30.0 grams, 0.12 mole) in the 500ml four-necked flask, sulfuric acid solution (260 milliliters, 0.73M), slowly heat up to 40 ℃ under stirring, add potassium bromate (total: 26.7 grams, 0.16 mole) in batches During the feeding period, the internal temperature is controlled not to exceed 55°C. After the addition, the temperature is raised to 65-70°C, and after 4 hours of heat preservation, the temperature is gradually lowered to 0-5°C, filtered, and the filter cake is washed with 500 ml of deionized water and 50 ml of acetone. After vacuum drying at 40°C, 28.0 g of a white solid was obtained, with a yield of 82.8%.

[0024] Melting point detected by capillary method: 224.5-225.8°C; 1 H NMR (300MHz, DMSO...

Embodiment 2

[0025] Embodiment 2: Synthesis of 1-hydroxyl-1,2-phenyliodyl-3(1H)-ketone

[0026] In the present embodiment, the principle of synthesizing 2-iodoylbenzoic acid is shown in the following formula:

[0027]

[0028] Concrete reaction condition is as follows:

[0029] Add 2-iodobenzoic acid (11.59 grams, 46.7 mmoles) in the 500ml four-necked flask, sodium periodate (10.0 grams, 46.7 mmoles), glacial acetic acid (97.94 grams) bath temperature is slowly warming up to 120 ℃ under magnetic stirring, The internal temperature rose to 110°C and began to reflux, kept at reflux for 4 hours, cooled naturally to room temperature, added deionized water (233 grams) under stirring and left to filter, and the filter cake was deionized water (100 ml x 3) and acetone (100 ml x 3) washing and vacuum drying at 40° C. to obtain 10.58 g of a white solid with a yield of 85.8%.

[0030] Melting point detected by capillary method: 212.1-216.0°C; 1 H NMR (300MHz, DMSO-d 6 ), δ8.095-7.945 (m, 3H); ...

Embodiment 3

[0031] Embodiment 3: Synthesis of 2-iodoxybenzoic acid (IBX) research

[0032] In the present embodiment, the principle of synthesizing 2-iodoylbenzoic acid is shown in the following formula:

[0033]

[0034] Concrete reaction condition is as follows:

[0035] Add 2-iodobenzoic acid (50.0g, 0.20 mole) in the 1000ml three-necked flask, sulfuric acid solution (450ml, 0.73M or 1.10M or 1.40M), after stirring evenly, add potassium persulfate (70g, or 80 grams, or 90 g or 100 g, 0.26 mole or 0.30 mole or 0.33 mole or 0.37 mole), the mixture was warmed to about 50 ° C within 20 minutes, and then potassium persulfate (70 g, or 80 g, or 90 g or 100 g, 0.26 mole or 0.30 mol or 0.33 mol or 0.37 mol), after the addition, the temperature was raised to about 70°C, and stirred at this temperature for 4 or 6 hours. It was then cooled to 0-5°C and stirred slowly at this temperature for 2 hours. After filtration, the resulting solid was washed with water (600 mL) and acetone (600 mL), a...

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Abstract

The invention relates to a method for preparing 2-iodoxybenzoic acid, and belongs to the technical field of synthesis of rings containing a halogen atom as a heterocyclic atom. The method comprises the following steps: adding an oxidant to 2-iodobenzoic acid used as a raw material, carrying out a reaction in an acidic solution at 50-120 DEG C for 1-6 h, and purifying the obtained reaction productto obtain the 2-iodoxybenzoic acid. The method has the advantages of small toxicity, mild technologic conditions, economical and cheap property and suitableness for industrialization when applied to the synthesis of a catalyst.

Description

technical field [0001] The application relates to a method for preparing 2-iodoxybenzoic acid, which belongs to the technical field of synthesis of rings containing halogen atoms as heterocyclic atoms. Background technique [0002] In organic synthesis, the oxidation of alcohols to ketones has always been an important and widely used reaction type. High-valent chromium reagents such as PCC, PDC, and high-valent manganese reagents such as manganese dioxide can oxidize alcohols to ketones, but these heavy metal reagents have disadvantages such as high toxicity, high pollution, and uneconomical, which limit their industrial applications, especially It is in the field of synthesis of medicine, pesticide and fine chemicals. In this context, organic chemists have developed some greener alcohol oxidation methods, and hypervalent iodine reagent is one of the more important ones. [0003] 2-iodyl benzoic acid (IBX) is one of the high iodine reagents discovered the earliest, because...

Claims

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Application Information

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IPC IPC(8): C07D347/00
CPCC07D347/00
Inventor 薛汝强周志奎常娜王欣顾兴隆王继宽吕佳仪吴娇徐龙飞马远梅晶晶付君平秦欣荣王兆刚邱家军
Owner ZHEJIANG GUOBANG PHARMA