Preparation method for aromatic carboxylic acid compounds
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
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
View PDF2 Cites 4 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
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
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
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%.
[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%.
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
PUM
Login to view more
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
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to view more 
Login to view more