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Method for preparing ibuprofen

A technology of isobutylphenyl and isobutylbenzene, which is applied in the synthesis field of medicine ibuprofen (propionic acid), and achieves the effects of reducing the amount of three wastes, high yield and cheap raw materials

Inactive Publication Date: 2009-06-17
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method needs to use the noble metal Pd catalyst, and there is also the problem of catalyst recovery.

Method used

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  • Method for preparing ibuprofen
  • Method for preparing ibuprofen
  • Method for preparing ibuprofen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 300g of isobutylbenzene (excess) and 40.5g (0.3mol) of anhydrous aluminum chloride into a 500mL three-neck flask with a stirring and reflux tube, cool down to 0°C, and add 27.5g (0.35mol) of acetyl chloride dropwise while stirring, After 2 hours of addition, reflux reaction for 2 hours after the addition, cooling down after the reaction, pour the reaction solution into 500mL of ice water, separate the phases, and rectify the organic phase at normal pressure to recover 260g of excess isobutylbenzene to obtain 4-isobutylphenylethyl Ketone liquid 51.7g, content≥99.0% (gas chromatography, area normalization method).

[0029] Add 38g (0.30mol) of dimethyl sulfate, 20.0g (0.32mol) of dimethyl sulfide and 20)0mL of petroleum ether into a 500mL three-neck flask with a stirring and reflux tube, stir at 40°C for 2h, then add 4-isobutyl Base acetophenone liquid 52.0g (0.295mol) and potassium hydroxide 18g (0.32mol), reflux stirring reaction 7h, reaction finishes cooling, adds ...

Embodiment 2

[0031] Prepare 4-isobutyl acetophenone with example 1.

[0032] Add 40.5g (0.32mol) of dimethyl sulfate, 20.5g (0.33mol) of dimethyl sulfide and 200mL of petroleum ether into a 500mL three-necked flask with a stirring and reflux tube, stir at 40°C for 2h, then add 4-isobutyl 52g (0.295mol) of acetophenone liquid and 18g (0.32mol) of potassium hydroxide were refluxed and stirred for 9h. After the reaction was completed, the temperature was lowered, and hydrochloric acid was added for neutralization, phase separation, and the solvent was recovered by negative pressure distillation to obtain 2-(4-isobutyl phenyl)-1,2-propylene oxide yellow solid 55.2g, content≥98.8% (gas chromatography, area normalization method).

[0033] Add 38.1g (0.20mol) of 2-(4-isobutylphenyl)-1,2-propylene oxide, 0.4g of anhydrous zinc chloride, and 100mL of cyclohexanone into a 250mL three-necked flask with a stirring and drying tube, Stir at 0° C. for 4 h, after the reaction is complete, add 100 mL of w...

Embodiment 3

[0035] Prepare 4-isobutyl acetophenone with example 1.

[0036] Add 42.9g (0.34mol) of dimethyl sulfate, 23g (0.35mol) of dimethyl sulfide and 200mL of petroleum ether into a 500mL three-necked flask with a stirring and reflux tube, stir at 40°C for 2h, then add 4-isobutylbenzene 52g (0.295mol) of ethyl ketone liquid and 18g (0.32mol) of potassium hydroxide, refluxed and stirred for 10h, cooled down after the reaction, added hydrochloric acid for neutralization, phase separation, and vacuum distillation to recover the solvent to obtain 2-(4-isobutyl Phenyl)-1,2-propylene oxide yellow solid 55.4g, content ≥ 98.5% (gas chromatography, area normalization method).

[0037] Add 38.1g (0.20mol) of 2-(4-isobutylphenyl)-1,2-propylene oxide, 1.0g of anhydrous tin chloride, and 100mL of cyclohexanone into a 250mL three-necked flask with a stirring and drying tube, Stir at 20° C. for 2 h, after the reaction is complete, add 100 mL of water to wash and separate the phases. The organic ph...

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Abstract

The invention provides a method for preparing ibuprofen. The method comprises: taking isobutyl-benzene as raw material, obtaining 4-isobutyl acetophenone by Friedel-Crafts reaction, obtaining 2-(4-isobutyl phenyl group)-1, 2-propylene oxide by epoxidation, obtaining 1-(4-isobutyl phenyl group) propionaldehyde through intramolecular rearrangement in the presence of Lewis acid catalysis, and obtaining the ibuprofen by oxidation of hydrogen peroxide. The preparation method has the advantages of nonuse of noble metal catalyst, low-priced material, simple process, mild reaction condition, high yield and little amount of the three wastes, and solvent used in the method meets industrialized requirements.

Description

technical field [0001] The invention relates to a method for synthesizing medicine ibuprofen (2-(4-isobutylphenyl) propionic acid). Background technique [0002] Ibuprofen (2-(4-isobutylphenyl)propionic acid, 1), Ibuprofen is an anti-inflammatory, antipyretic and pain-relieving OTC product, and is one of the most common non-steroidal anti-inflammatory drugs (NSAIDs) in clinical use. First, it is widely used by doctors to treat rheumatism or rheumatoid diseases, as well as joint and muscle pain, headache, dysmenorrhea and other pains. Ibuprofen was launched in the UK in 1966 and in the US in 1974. In 1983, ibuprofen became the first NSAID that could be sold over-the-counter in the UK, and in 1984, ibuprofen became an over-the-counter drug in the United States. Ibuprofen is a non-selective cyclooxygenase (COX) inhibitor, and its anti-inflammatory properties are achieved by regulating leukocyte activity, reducing cytokine production, inhibiting free radicals and signal transd...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C57/30C07C51/235
Inventor 陈平刘春华黄鹏勉曹忠曾蒲霓
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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