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Preparation method for aromatic carboxylic acid compounds

A technology for aromatic carboxylic acids and compounds, which is applied in the field of organic synthesis and can solve the problems of expensive catalysts and ligands

Active Publication Date: 2012-03-14
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The palladium-catalyzed reaction of carbon monoxide and aryl halides to synthesize aromatic carboxylic acids under mild reaction conditions has been successfully developed and has high reaction efficiency, but the catalysts and ligands are expensive

Method used

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  • Preparation method for aromatic carboxylic acid compounds
  • Preparation method for aromatic carboxylic acid compounds
  • Preparation method for aromatic carboxylic acid compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1, the preparation of p-toluic acid

[0049] Add cuprous iodide (0.2mmol, 38mg), L-proline (0.2mmol, 23mg), Cs 2 CO 3 (2mmol, 652mg), p-methyliodobenzene (1mmol, 218mg), malononitrile (2mmol, 132mg) and solvent dimethyl sulfoxide (1mL), the pH value of the reaction system is 10, at 140 ° C, in the air In the presence of conditions, react for 48 hours; after the reaction is completed, cool to room temperature, remove the solvent dimethyl sulfoxide with a rotary evaporator, add 2 mL of 1M hydrochloric acid (pH = 2 ~ 3) for acidification, and then use ethyl acetate The ester was extracted 3 times, 2 mL each time, the combined organic phase was concentrated, and purified with a silica gel column (the specification of silica gel was 200-300 mesh, and the eluent was petroleum ether / ethyl acetate (3:1, v / v )) to obtain p-toluic acid 75mg, the productive rate was 55%.

[0050] Product p-toluic acid: 1 H NMR (CDCl 3 , 600MHz, ppm) δ12.59(s, br, 1H), 7.93(d, 2H, J...

Embodiment 2

[0051] Embodiment 2, the preparation of p-toluic acid

[0052] Proceed according to the steps described in Example 1, but replace cesium carbonate with potassium carbonate as the base, and the yield of p-toluic acid is 49%.

Embodiment 3

[0053] Embodiment 3, the preparation of p-toluic acid

[0054] Carry out according to the procedure described in Example 1, but replace cesium carbonate with potassium phosphate as the base, and the yield of p-toluic acid is 45%.

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Abstract

The invention discloses a preparation method for aromatic carboxylic acid compounds. According to the method, corresponding aromatic carboxylic acid compounds are obtained by reacting aryl halides with malononitrile under the conditions of alkali and a copper catalyst. A ligand cocatalyst is also used in the method and is one selected from the group consisting of 2-pipecolic acid, 2-picolinic acid, 2-pralidoxime, glyoxime, 1,10-orthophenanthrolene, N,N-dimethylethylenediamine and L-proline. Compared to the method of oxidation of substituted aromatic hydrocarbons, the method of directly reacting Grignard reagents and organic lithium reagents with carbon dioxide and the method of reacting the compounds of aryl zinc and aryl boron with carbon dioxide under catalysis of transition metals in the prior art, the method provided in the invention has following obvious advantages: the method is based on aryl halides which are easily available; a cheap copper salt is used as a catalyst; little environmental pollution and high yield are realized; high tolerance of a plurality of function groups on aromatic rings is obtained; separation and purification are convenient; etc.

Description

technical field [0001] The invention relates to a preparation method of an aromatic carboxylic acid compound, belonging to the field of organic synthesis. Background technique [0002] Aromatic carboxylic acids not only have the properties of esterification, acid halide, amidation, anhydride formation, and salt formation of fatty acids, but also can undergo substitution, addition, and ring cracking reactions on the aromatic ring. Aromatic carboxylic acids are mostly prepared by oxidation of corresponding aromatic hydrocarbons, and can also be prepared by hydrolysis of aromatic nitriles and oxidation of aromatic alcohols and aromatic aldehydes. There are also a few extracted from natural products such as plants, wood, coal, and charcoal. Aromatic carboxylic acid derivatives are similar to aliphatic carboxylic acid derivatives, including metal salts, esters, acyls, halides, amides, anhydrides, etc. Due to the complex structure of aromatic carboxylic acid derivatives substitu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/08C07C51/08C07C63/04C07C65/21C07C63/36C07C63/331C07C63/70C07C63/24C07C63/26C07D319/18C07D333/40
Inventor 付华杨道山杨海军
Owner TSINGHUA UNIV
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