Unlock instant, AI-driven research and patent intelligence for your innovation.
Synthesis method of succinic acid derivative or 3-aryl propionic acid
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
An arylpropionic acid and a synthesis method technology, applied in the directions of organic chemistry methods, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of low atom economy, excessive oxidation, complicated operation, etc., and achieve good industrial application Prospects, mild reaction conditions, cheap and readily available raw materials
Active Publication Date: 2020-10-16
SICHUAN UNIV
View PDF4 Cites 3 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
In the above method, catalytic hydrogenation and carboxylation of aryl vinyl require high pressure, high requirements for reaction equipment, and need expensive catalysts to realize; the method of chromate oxidation of propylbenzene has problems such as waste of oxidant and excessive oxidation; The synthesis of 3-arylpropionic acid from diethyl benzylmalonate is cumbersome and the atom economy is not high; while the carboxylation reaction of aryl vinyl is often accompanied by the generation of α-carboxylated by-products
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 one: Synthesis of succinic acid derivatives
[0049] The synthetic reaction formula of succinic acid derivative is shown in formula (III),
[0050]
[0051] The synthesis of succinic acid derivatives comprises the following steps:
[0052] S1: Transfer the dry Schlenk tube (10 mL) with magnets into the glove box, add sodium tert-butoxide (48 mg, 0.5 mmol, 2.5 times equivalent);
[0053] S2: Take the Schlenk tube out of the glove box and connect it to the 2 On the double-row tube of the steel cylinder, under the condition that the Schlenk tube is closed, the double-row tube is pumped with CO 2 At least 3 times, excluding N in branch 2 , so that it is filled with CO 2 gas;
[0054] S3: in CO 2 NMP (2 mL), tert-butanol (38 μL, 0.4 mmol, 2 equivalents), 2,4,6-triisopropylthiophenol (95 mg, 0.4 mmol, 2 equivalents) and the reaction substrate ( 1) (0.2mmol);
[0055] S4: Seal the Schlenk tube and place it under liquid nitrogen. After it is completely fro...
Embodiment 2
[0101] Embodiment two: Synthesis of 3-aryl propionic acid
[0102] The synthetic reaction formula of 3-aryl propionic acid is shown in formula (II),
[0103]
[0104] The synthesis of 3-aryl propionic acid comprises the following steps:
[0105]S1: Transfer the dry Schlenk tube (10 mL) with the magneton into the glove box, add sodium tert-butoxide (48 mg, 0.5 mmol, 2.5 times equivalent);
[0106] S2: Take the Schlenk tube out of the glove box and connect it to the 2 On the double-row tube of the steel cylinder, under the condition that the Schlenk tube is closed, the double-row tube is pumped with CO 2 At least 3 times, excluding N in branch 2 , so that it is filled with CO 2 gas;
[0107] S3: in CO 2 Add NMP (2 mL), tert-butanol (38 μL, 0.4 mmol, 2 equivalents), 4-tert-butylthiophenol (66.5 mg, 0.4 mmol, 2 equivalents) and reaction substrate (3) (0.2 mmol);
[0108] S4: Seal the Schlenk tube and place it under liquid nitrogen. After it is completely frozen, open th...
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 synthesis method of a succinic acid derivative or 3-aryl propionic acid. The method comprises the following steps of: adding alkali into a dry reaction tube, adding a solvent, thiophenol and olefin under the atmosphere of CO2, carrying out reaction under the irradiation of visible light, quenching a mixture obtained by reaction after the reaction of raw materials is finished, and then performing separating and purifying to obtain the succinic acid derivative or the 3-aryl propionic acid product; wherein the alkali comprises sodium tert-butoxide, potassium tert-butoxide, lithium tert-butoxide and potassiumcarbonate; the thiophenol comprises 4-tert-butyl thiophenol and 2, 4, 6-triisopropyl thiophenol; the reaction substrate comprises an acrylate compound or an arylethylene compound. According to the method, the succinic acid derivative and 3-aryl propionic acid can be efficiently and highly selectively synthesized under the induction of visible light and the participation of CO2; according to the scheme, reaction conditions are mild, reaction substrate selectivity is wide, and amplification to a gram-level scale is achieved; raw materials used in the method are cheap and easily available, and the method has good industrial application prospects.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of succinic acid derivatives or 3-aryl propionic acid. Background technique [0002] The synthesis method of succinic acid mainly contains six categories: one is the catalytic oxidation of paraffin; the other is the catalytic hydrogenation of maleic anhydride or fumaric acid; the third is the carbonylation of acrylic acid. Generate succinic acid; the fourth is to use acetylene, carbon monoxide and water in the presence of cobalt catalyst to react in acidic medium to produce succinic acid; the fifth is to oxidize maleic acid or maleic anhydride by electrolysis; the sixth is biological fermentation method. In above-mentioned six kinds of methods, except biofermentation method and electrolysis method, all the other methods all need to use precious metal catalyst and high temperature, the condition is harsh; In addition, acrylic acid carbonyla...
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