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Preparation method of aryl propionic acid compound

A technology for aryl propionic acid compounds and compounds, which is applied in the field of preparation of aryl propionic acid compounds, and can solve problems such as carbonylation selectivity and difficulty in separation

Active Publication Date: 2020-09-22
ZHEJIANG NHU CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this carbonylation reaction, impurity linear isomer 3-[4-(2-methylpropyl)phenyl]propionic acid (English abbreviation: 3-IPPA) may be generated as shown in process (2). ), its content is usually >1%, that is, there is a problem of carbonylation selectivity
Due to the similar properties of the impurity linear isomer 3-IPPA and ibuprofen, it is difficult to separate by conventional methods

Method used

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  • Preparation method of aryl propionic acid compound
  • Preparation method of aryl propionic acid compound
  • Preparation method of aryl propionic acid compound

Examples

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preparation example Construction

[0042] The preparation method of described aryl propionic acid compound comprises the following steps:

[0043] S1, providing a substituted arylbenzene, and performing an acetylation reaction on the substituted arylbenzene to obtain an α-substituted aryl ethyl ketone;

[0044] S2, performing a hydrogenation reduction reaction on the α-substituted aryl ethyl ketone to obtain α-substituted aryl ethanol;

[0045] S3. In an acidic solution, carbon monoxide gas is introduced into the α-substituted arylethanol, and a carbonylation reaction is carried out under the co-catalysis of the main catalyst and the co-catalyst to obtain aryl propionic acid compounds.

[0046] In step S1, the process of the acetylation reaction can be represented by the following reaction formula:

[0047]

[0048] Preferably, hydrogen, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, C6-C24 One of aryl or substi...

Embodiment 1

[0088] The present embodiment provides the preparation method of ibuprofen, concretely carries out according to the following steps:

[0089] (S1) isobutylbenzene carries out acetylation reaction, obtains 4-isobutylacetophenone, specifically as follows:

[0090] Add 293.26g of anhydrous aluminum chloride and 536.80g of dichloromethane into the dry four-neck flask, control the temperature 99% and a yield of 97%.

[0091] (S2) 4-isobutylacetophenone (abbreviated as IBAP) is subjected to hydrogenation reduction reaction to obtain 1-(4-isobutyl-phenyl)-ethanol (abbreviated as IBPE), as follows:

[0092] Add IBAP (120g, 0.68 mol), 5% Pd / C catalyst (6g, 0.00283 mol), 120g of methanol into a 500mL autoclave, stir and mix, and replace the reactor with nitrogen for three times, and then with hydrogen. Three times, and finally filled with hydrogen to 1.0MPa, started stirring, and controlled the temperature at 30°C for hydrogenation reaction. During the reaction process, the conversion...

Embodiment 2- Embodiment 11

[0099] Embodiment 2 to embodiment 11 are on the basis of embodiment 1, change the kind and the amount of palladium compound and phosphine ligand in the main catalyst of step (S3), cocatalyst and other conditions are the same as embodiment 1, specifically as shown in the following table . Its final TOF value, conversion rate, selectivity reaction result are also shown in table 1 below:

[0100] Table 1

[0101]

[0102] As seen from Table 1, in embodiment 7-embodiment 11, when the mol ratio of palladium compound, phosphine ligand and 1-(4-isobutyl-phenyl)-ethanol i.e. IBPE in the main catalyst is at 1:6:15000- Within the range of 1:10:20000, its TOF value, conversion rate, and selectivity are all better, which also verifies the preferred range mentioned earlier in this application.

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Abstract

The invention provides a preparation method of an aryl propionic acid compound, wherein the preparation method comprises the following steps: carrying out acetylation reaction on substituted aryl benzene to obtain aryl acetophenone; carrying out hydrogenation reduction reaction on alpha-substituted aryl ethyl ketone to obtain alpha-substituted aryl ethanol; and in an acidic solution, introducing carbon monoxide gas into the alpha-substituted aryl ethanol, and carrying out a carbonylation reaction under the co-catalytic action of a main catalyst and a cocatalyst to obtain the aryl propionic acid compound, wherein the cocatalyst has the following structural formula described in the specification, R1 is one of hydrogen and a substituted carboxylic acid group, and R2 is one of hydrogen, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C3-C12 naphthenic base, substituted carbonyl containing C6-C24 aryl or substitutedaryl, substituted carbonyl containing C3-C12 heterocyclic radical or substituted heterocyclic radical, phenyl, substituted phenyl, naphthyl and substituted naphthyl.

Description

technical field [0001] The invention relates to the field of synthesis of aryl propionic acid compounds, in particular to a preparation method of aryl propionic acid compounds. Background technique [0002] Compared with traditional antipyretic and analgesic drugs such as aspirin, arylpropionic acid non-steroidal anti-inflammatory analgesics have excellent antipyretic, analgesic and anti-inflammatory effects, significant curative effect and small side effects, and have been rapidly developed and applied in recent years. Ibuprofen, as one of the important varieties, is widely used in the treatment of rheumatoid arthritis, rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis. Ibuprofen can be prepared by a three-step catalytic method, as shown in the process (1) of the following formula: [0003] [0004] The method has the characteristics of simple synthesis, no need to use a large amount of solvent, and avoiding a large amount of three wastes, and has the cha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/12C07C57/30C07C59/64C07C59/86C07C59/84C07D333/22B01J31/24B01J31/22
CPCC07C51/12C07C45/46C07C29/145C07D333/22B01J31/2409B01J31/2239C07C2601/08B01J2531/824C07C57/30C07C49/76C07C33/20C07C59/64C07C59/86C07C59/84Y02P20/584
Inventor 刘金龙黄顺礼韩润泽楼坚聪吴仔剑王晓春汪紫玉
Owner ZHEJIANG NHU CO LTD
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