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Method for preparing 2-(4-isobutylphenyl)propionate from 1-(4-isobutylphenyl)ethanol

A technology of isobutylphenyl and propionate, which is applied in the preparation of carboxylate, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of difficult recovery and reuse of catalysts, high price, etc.

Active Publication Date: 2014-11-05
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The purpose of the present invention is to overcome the disadvantages that the existing hydroesterification reaction homogeneous catalytic system catalyzer uses expensive Pd noble metal and toxic phosphine ligand, and the catalyzer is difficult to recycle and reuse, and provides a kind of 1-( Method for preparing 2-(4-isobutylphenyl)propionate by hydroesterification of 4-isobutylphenyl)ethanol

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 20mL of solvent n-hexane, 2g of imidazole, 12g of ethylene oxide into a 75mL deep-frozen stainless steel autoclave, and use nitrogen (N 2 ) was replaced three times, stirred at room temperature for 2h, and then reacted at 60°C for 5h. After the reaction was over, the solvent was removed under reduced pressure to constant weight to obtain 3-polyethylene glycol imidazole (L 1 ), calculated by mass balance According to n (chlorobutane): n (L 1 )=5:1, the reactants were added to the autoclave, N 2 After replacing three times, the pressure was raised to 0.6MPa, heated in a water bath at 90°C for 10 hours, and distilled under reduced pressure to obtain chloro-1-butyl-3-polyethylene glycol imidazole (L 2 ). Added in the autoclave with L 2 Equimolar amount of homemade KCo(CO) 4 , 25°C, 2.0MPa CO, reacted for 4h to get dark green oily liquid [H(OCH 2 CH 2 )nbim]Co(CO) 4 catalyst.

[0017] In a 75mL stainless steel autoclave, add 1mL36% hydrochloric acid, 10mL n-hep...

Embodiment 2

[0019]The catalyst solution in the lower layer obtained by static stratification in Example 1 was transferred to a 75mL stainless steel autoclave, and 1mL36% hydrochloric acid, 10mL n-heptane, 0.51g imidazole (7.5mmol), 1.92g methanol (60mmol), 5.34 Put g1-(4-isobutylphenyl)ethanol IBPE (30mmol) into the kettle, replace with CO three times, pass CO to increase the pressure, start heating and stirring, keep the reaction temperature at 125-130°C, and the reaction pressure at 6.0MPa, and react for 16h. Cool after the reaction, and let stand to separate layers. The conversion of IBPE was 99.5%, and the yield of methyl 2-(4-isobutylphenyl)propionate was 85%.

Embodiment 3

[0021] The lower layer catalyst solution obtained by static layering in Example 2 was transferred to a 75mL stainless steel autoclave, and 1mL36% hydrochloric acid, 10mL n-heptane, 0.51g imidazole (7.5mmol), 1.92g methanol (60mmol), 5.34 g1-(4-isobutylphenyl)ethanol IBPE (30mmol), replaced with CO three times, started heating and stirring, kept the reaction temperature at 125-130°C, and the reaction pressure at 6.0MPa, and reacted for 16h. After the reaction was finished, it was cooled, and the reaction product was allowed to stand and separate into layers. The conversion rate of IBPE was 99.6%, and the yield of methyl 2-(4-isobutylphenyl)propionate was 85%.

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Abstract

The invention discloses a method for preparing 2-(4-isobutylphenyl)propionate from 1-(4-isobutylphenyl)ethanol (IBPE). According to the present invention, an imidazole functionalized ion liquid containing cobalt carbonyl and polyether is adopted as a catalyst to carry out a hydroesterification reaction of IBPE, carbon monoxide and an alkyl alcohol to prepare 2-(4-isobutylphenyl)propionate. The method has the following characteristics that: precious metal use is avoided, catalytic activity is good, and the catalysis system is easy to separate, and can be recycled.

Description

technical field [0001] The present invention relates to the synthetic field of pharmaceutical intermediates, in particular the present invention relates to a method for preparing 2-(4-isobutylphenyl)propionate from 1-(4-isobutylphenyl)ethanol (IBPE) . In the present invention, 1-(4-isobutylphenyl)ethanol is used as a raw material, and an imidazole functionalized ionic liquid containing cobalt carbonyl and polyether is used as a catalyst to prepare 2-(4-isobutyl) by hydroesterification of IBPE phenyl) propionate. Background technique [0002] Ibuprofen (Ibuprofen) is a new generation of important non-steroidal anti-inflammatory analgesic drugs. Since it was launched in the late 1970s, it has developed rapidly due to its high curative effect and small side effects, and has become the most produced and used drug. One of the anti-inflammatory antipyretic analgesics. At present, industrial production mainly adopts the Boots method or the Darsens method, and the published paten...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/24C07C67/08
CPCY02P20/584
Inventor 吕志果郭振美聂涛陈强王志会
Owner QINGDAO UNIV OF SCI & TECH
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