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Method for preparing 3, 7-diethyl nonane-4, 6-diketone

A technology of ethyl nonane and diketone, applied in the field of organic chemical synthesis, can solve the problems of harsh reaction conditions, low yield and the like, and achieve the effects of low cost, safe yield and mild reaction conditions

Active Publication Date: 2018-08-10
ASTATECH CHENGDU BIOPHARM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method has simple steps, the yield is low and the reaction conditions are harsh.

Method used

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  • Method for preparing 3, 7-diethyl nonane-4, 6-diketone
  • Method for preparing 3, 7-diethyl nonane-4, 6-diketone
  • Method for preparing 3, 7-diethyl nonane-4, 6-diketone

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Experimental program
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Effect test

Embodiment 1

[0026] S1. Ethylmagnesium bromide (700ml, 5.5eq) was added to a three-necked flask, and a tetrahydrofuran (100g) solution containing dimethyl isophthalate (50g, 1.0eq) was added dropwise at 0°C. After the dropwise addition, the temperature was naturally raised to 25°C, and the system reacted for 2.5-4 hours. After the reaction, the reaction system was slowly poured into an aqueous ammonium chloride solution, and the product 2-3 was extracted with ethyl acetate (1000g), and the organic phase was concentrated to dryness. The residue was recrystallized from n-heptane to obtain 3,3'-(1,3-phenylene)bis(3-pentanol) with a yield of 76.8%.

[0027] S2. Dissolve the above 3,3'-(1,3-phenylene)bis(3-pentanol) (10g, 1.0eq) in acetic acid (50g), pour it into an autoclave, add 10% Pd / C (0.5g), replace with hydrogen, make the internal pressure 1.0-2.0MPa, heat the external bath to 100°C, react for 16h, after the reaction is completed, cool, filter, wash the filter cake with petroleum ether, ...

Embodiment 2

[0031] S1. Ethylmagnesium bromide (420ml, 5.5eq) was added to a three-necked flask, and a solution of tetrahydrofuran (50g) containing dimethyl isophthalate (30g, 1.0eq) was added dropwise at 0°C. After the dropwise addition, the temperature was naturally raised to 25° C., and the system reacted for 2.5-4 hours. After the reaction, the reaction system was slowly poured into an aqueous ammonium chloride solution, and the product 2-3 was extracted with ethyl acetate (600 g), and the organic phase was concentrated to dryness. The residue was recrystallized from n-heptane to obtain 3,3'-(1,3-phenylene)bis(3-pentanol) with a yield of 74.2%.

[0032] S2. Dissolve the above 3,3'-(1,3-phenylene)bis(3-pentanol) (30g, 1.0eq) in acetic acid (250g), pour it into an autoclave, add 10% Pd / C (5.5g), replace with hydrogen, make the internal pressure 1.5-2.0MPa, heat the external bath to 100°C, react for 16h, after the reaction is completed, cool, filter, wash the filter cake with petroleum et...

Embodiment 3

[0036]S1. Ethylmagnesium bromide (700ml, 5.5eq) was added to a three-necked flask, and a tetrahydrofuran (100g) solution containing dimethyl isophthalate (50g, 1.0eq) was added dropwise at 0°C. After the dropwise addition, the temperature was naturally raised to 25°C, and the system reacted for 2.5-4 hours. After the reaction, the reaction system was slowly poured into an aqueous ammonium chloride solution, and the product 2-3 was extracted with ethyl acetate (1000g), and the organic phase was concentrated to dryness. The residue was recrystallized from n-heptane to obtain 3,3'-(1,3-phenylene)bis(3-pentanol) with a yield of 76.8%.

[0037] S2. Dissolve the above 3,3'-(1,3-phenylene)bis(3-pentanol) (30g, 1.0eq) in acetic acid (200g), pour it into an autoclave, add 10% Pd / C (4.5g), replace with hydrogen, make the internal pressure 1.3-1.6MPa, heat the external bath to 100°C, react for 18h, after the reaction is completed, cool, filter, wash the filter cake with petroleum ether, ...

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Abstract

The invention discloses a method for preparing 3, 7-diethyl nonane-4, 6-diketone, and belongs to the field of chemical synthesis. The 'method for preparing the 3, 7-diethyl nonane-4, 6-diketone' has the advantages that dimethyl isophthalate which is low in cost is used as a raw material for the 3, 7-diethyl nonane-4, 6-diketone, the 3, 7-diethyl nonane-4, 6-diketone can be prepared by the aid of four-step reaction including elimination and addition, catalytic hydrogenation reaction, Birch reduction and ozone oxidation, the method is low in cost, convenient to operate, high in yield and suitable for large-scale industrial production, includes short synthesis processes and is safe, and reaction conditions are mild.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a preparation method of 3,7-diethylnonane-4,6-dione. Background technique [0002] 3,7-diethylnonane-4,6-dione is widely used as a coating for electronic components, but the synthesis methods reported at home and abroad have certain defects. [0003] In 1951, Eugene H.Man et al. reported a synthetic 3,7-diethyl The method of diethylnonane-4,6-dione, the method is to adopt 2-ethylbutyric acid as starting material, and obtain 3,7-diethylnonane-4,6-dione through six-step reaction . Although this method is easy to operate in each step, it has many process steps and intermediate 6 is difficult to purify due to its low boiling point; the last step reaction itself is more complicated, the phenol produced by the reaction is not easy to remove, and the final product is extremely difficult to purify and has a low yield. The reaction formula is as follows: [0004] [0005] ...

Claims

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Application Information

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IPC IPC(8): C07C49/12C07C45/40C07C5/11C07C13/23C07C1/22C07C15/02C07C29/36C07C33/26
CPCC07C1/22C07C5/11C07C29/36C07C45/40C07C2523/04C07C2523/44C07C2601/16C07C33/26C07C15/02C07C13/23C07C49/12
Inventor 陈孝刚庄明晨柯东磊罗建业郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP
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