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Synthesis method of 4-methyl-(2, 4, 4-trimethylpentyl)-2H-pyran-2-one

The technology of a trimethylpentyl group and a synthetic method is applied in the field of synthesis of oxypiroxolactone, which can solve the problems of high requirements for reaction conditions, high requirements for equipment, low reaction yield, etc., and achieve low cost of process raw materials and high synthesis efficiency. The effect of no pollution in the route and mild reaction conditions

Pending Publication Date: 2021-10-12
CHENGDU ORGANOCHEM CO LTD
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  • Claims
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Problems solved by technology

[0005] The conditions of the ring-closing process in the existing above-mentioned steps have the following several kinds: (1) carry out ring-closing reaction with sulfuric acid, acetic acid solution, but this method carbonization is serious, and reaction yield is low; (2) under the situation that does not use catalyzer Directly close the ring at a high temperature of 200°C. This method has high requirements for reaction conditions and high process risk. At the same time, the method adopts rectification equipment and has high requirements for industrial equipment; (3) The ring closing process adopts a two-step method. First Hydrolyze ketoacid methyl ester to obtain ketoacid, then ketoacid is lactonized in acetic acid solvent under the catalysis of concentrated sulfuric acid to obtain cyclization product pyrone, but this method needs to use sulfuric acid and acetic acid solution, serious carbonization, and requires two Only one step can get pyrone, the route is long, the industrial route is complicated, and the industrial waste water is produced a lot. Based on this, this patent application is proposed

Method used

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  • Synthesis method of 4-methyl-(2, 4, 4-trimethylpentyl)-2H-pyran-2-one
  • Synthesis method of 4-methyl-(2, 4, 4-trimethylpentyl)-2H-pyran-2-one
  • Synthesis method of 4-methyl-(2, 4, 4-trimethylpentyl)-2H-pyran-2-one

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Embodiment 1

[0028] Embodiment 1: A kind of synthetic method of 4-methyl-(2,4,4-trimethylpentyl)-2H-pyran-2-one

[0029] Take a 500ml three-necked flask, install a thermometer and a condenser tube, then add 125ml of dichloromethane and 46.15g of isononanoyl chloride (0.26mol, 1.2eq) in sequence, cool down to -9°C, and add 73.00g of aluminum trichloride in one go at this temperature (0.55mol, 2.5eq), at this time, there was a significant temperature rise in the three-necked flask, and the reaction system was a light yellow suspension. After stirring at room temperature for 30min, 25.0g (0.22mol, 3,3-methyl methacrylate) was quickly added dropwise. 1.0eq), the addition is completed, the system is refluxed at an external temperature of 40°C, and the internal temperature is 37°C. After HPLC detects that the acylation reaction intermediate M1 is completely generated, the reaction system is poured into 200ml of ice water, stirred and separated, and the organic phase is passed through Washed with...

example 2

[0031] Example 2: A synthetic method of 4-methyl-(2,4,4-trimethylpentyl)-2H-pyran-2-one

[0032] Take a 500ml three-necked flask, install a thermometer and a condenser tube, then add 125ml of dichloromethane and 46.15g of isononanoyl chloride (0.26mol, 1.2eq) in sequence, cool down to -9°C, and add 73.00g of aluminum trichloride in one go at this temperature (0.55mol, 2.5eq), at this time, there was a significant temperature rise in the three-necked flask, and the reaction system was a light yellow suspension. After stirring at room temperature for 30min, 25.0g (0.22mol, 3,3-methyl methacrylate) was quickly added dropwise. 1.0eq), the addition is complete, the system is refluxed at an external temperature of 40°C, and the internal temperature is 37°C. After HPLC detects that the intermediate M1 is completely formed, the reaction system is poured into 200ml of ice water, stirred and separated, and the organic phase is treated with 1N hydrochloric acid Washed with water and once...

example 3

[0034] Example 3: A synthetic method of 4-methyl-(2,4,4-trimethylpentyl)-2H-pyran-2-one

[0035] Take a 500ml three-necked flask, install a thermometer and a condenser tube, add 125ml of dichloromethane, 46.15g of isononanoyl chloride (0.26mol, 1.2eq) in sequence, cool down to -9°C, and add aluminum trichloride (73.00g , 0.55mol, 2.5eq), there was an obvious temperature rise in the three-necked flask, and the system was a light yellow suspension. After stirring at room temperature for 30 minutes, 25.0g (0.22mol, 1.0eq) of 3,3-methyl methacrylate was quickly added dropwise After the addition, the system was refluxed at an external temperature of 40°C, and the internal temperature was 37°C. After the intermediate M1 was completely formed by HPLC, the reaction system was poured into 200ml of ice water, stirred and separated, the organic phase was washed with 1N hydrochloric acid, purified water After washing once, drying over anhydrous sodium sulfate, and concentrating the organi...

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Abstract

The invention discloses a synthesis method of 4-methyl-(2, 4, 4-trimethylpentyl)-2H-pyran-2-one, which comprises the following steps: S1, by taking 3, 3-methyl methacrylate and isononanoyl chloride as raw materials and dichloromethane as a solvent, carrying out Friedel-Crafts acylation reaction under the action of Lewis acid to obtain an intermediate M1; and s2, adding the intermediate M1 into a reaction container, adding an organic solvent, stirring and dissolving, adding calcium oxide, carrying out ring closing reaction at 20-120 DEG C, cooling, filtering and purifying to obtain a target product. The method has the advantages of low process raw material cost, no need of concentrated sulfuric acid and acetic acid solution, realization of direct ring closing reaction of calcium oxide in alcohol or ether solution at 20-120 DEG C to obtain the lactone, mild reaction conditions, short synthesis route, no pollution, high product purity, high yield and high product purity. The problems of tedious technical route, difficult operation, high danger, high cost, pollution and low yield and purity of the existing synthesis technology of the hydroxypiperidone intermediate are solved.

Description

technical field [0001] The invention relates to the technical field of oxypiroxolactone synthesis, in particular to a synthesis method of 4-methyl-(2,4,4-trimethylpentyl)-2H-pyran-2-one. Background technique [0002] Pyrone is an important intermediate for the preparation of oxypyrone. Oxypirone has an excellent antipruritic effect, has a unique effect on eliminating skin itching, can effectively kill fungi that grow on the skin, and has a special deodorizing effect. Good compounding, safe, non-toxic, non-irritating, it is an ideal high-efficiency fungicide, widely used in shampoo, hair care, body wash, cosmetics, skin care products, washing products. Therefore the synthetic method of pyrone is also particularly important. [0003] The existing synthetic method of pyrone is first to use 3,3-methyl methacrylate and isononanoyl chloride as raw materials to carry out acylation reaction to obtain intermediate M1: 3,7,9,9-tetramethyl-2 -Decene-5-keto acid methyl ester, then 3,7...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/38
CPCC07D309/38Y02P20/55
Inventor 邓倩谈平忠王利民郑守军
Owner CHENGDU ORGANOCHEM CO LTD
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