Preparation method for alpha-hydroxy cyclo-pentadecanone

A kind of technology of cyclopentadecanone, alkyl pentadecanediamide

Inactive Publication Date: 2017-05-17
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned method has many by-products, and it is difficult to separate and purify

Method used

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  • Preparation method for alpha-hydroxy cyclo-pentadecanone
  • Preparation method for alpha-hydroxy cyclo-pentadecanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 40mL of dry xylene to a 250mL dry four-neck flask equipped with a stirring, thermometer, condenser, and dropping funnel, add 1.60g (0.07mol) of sodium metal to the flask, and slowly raise the temperature to 2 Boil the toluene, stir rapidly for 5 minutes, and beat the sodium into silvery white fine particles. Control the temperature at 100°C, slowly add dropwise 40mL xylene solution dissolved with 3.82g (0.01mol) N,N,N',N'-tetraethylpentadecanediamide, after 4 hours of dropwise addition, keep warm React for 2 hours. After the reaction was completed, 8 mL of absolute ethanol was added dropwise to decompose the remaining metallic sodium. The insoluble matter was removed by filtration, the filtrate was washed with water until neutral, and the solvent was distilled off under reduced pressure to obtain 2.64 g of a crude product. The reaction product was analyzed by gas chromatography, and the content of α-hydroxycyclopentadecone was 90.8%.

Embodiment 2

[0027] Add 40ml of dry toluene to a 250ml dry four-neck flask equipped with stirring, thermometer, condenser and dropping funnel, add 1.60g (0.07mol) sodium metal to the flask, and slowly raise the temperature until the toluene boils under the protection of nitrogen , stirred rapidly for 5 minutes, and beat the sodium into silvery white fine particles. Control the temperature at 90°C, add dropwise 40ml of toluene solution dissolved with 4.38g (0.01mol) N,N,N',N'-tetrapropylpentadecanediamide, after 4 hours of dropwise addition, keep warm for 3 Hour. After the reaction was completed, 8 mL of absolute ethanol was added dropwise to decompose the remaining metallic sodium. The insoluble matter was removed by filtration, the filtrate was washed with water until neutral, and the solvent was distilled off under reduced pressure to obtain 2.68 g of a crude product. The reaction product was analyzed by gas chromatography, and the content of α-hydroxycyclopentadecone was 89.3%.

Embodiment 3

[0029] Add 40ml of dry benzene to a 250ml dry four-neck flask equipped with stirring, thermometer, condenser and dropping funnel, add 2.30g (0.10mol) sodium metal to the flask, and slowly raise the temperature until the benzene boils under the protection of nitrogen , stirred rapidly for 5 minutes, and beat the sodium into silvery white fine particles. Control the temperature at 80°C, add dropwise 40ml of benzene solution in which 4.94g (0.01mol) N,N,N',N'-tetrabutylpentadecanediamide is dissolved, and after 5 hours of dropwise addition, keep warm for 5 Hour. After the reaction was completed, 8 mL of absolute ethanol was added dropwise to decompose the remaining metallic sodium. The insoluble matter was removed by filtration, the filtrate was washed with water until neutral, and the solvent was distilled off under reduced pressure to obtain 2.70 g of a crude product. The reaction product was analyzed by gas chromatography, and the content of α-hydroxycyclopentadecone was 88....

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Abstract

The invention discloses a preparation method for alpha-hydroxy cyclo-pentadecanone. The method comprises the following steps of: adding a defined amount of dry organic solvent and metallic sodium into a dry reaction device which is equipped with a thermometer, a stirrer, a reflux condensing tube and a dropping funnel; increasing the temperature and boiling the solvent under N2 protection, quickly stirring and breaking the metallic sodium into fine particles; heating the reaction system to a certain temperature, and then slowly dropwise adding N,N,N',N'-tetra-alkyl pentadecane diamide dissolved in the dry organic solvent into the reaction device; after completely dropwise adding, keeping the temperature and reacting for a period of time; after the ending of the reaction, dropwise adding a defined amount of absolute ethyl alcohol and removing the remaining metallic sodium; after the metallic sodium is completely decomposed, filtering and removing the undissolved substances; washing the filtrate with water till becoming neutral; and drying the solvent by rotating, thereby acquiring a crude product of alpha-hydroxy cyclo-pentadecanone. According to the invention, the N,N,N',N'-tetra-alkyl pentadecane diamide is taken as a raw material for acyloin condensation, so that the method has the advantages of high product yield, high purity and suitability for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a method for preparing α-hydroxycyclopentadecone by using N,N,N',N'-tetraalkylpentadecanediamides. Background technique [0002] (R)-Muskone is the main functional component of natural musk, and its chemical name is (R)-3-methylcyclopentadecanone. (R)-Muskone has some important pharmacological effects of natural musk, and has important medicinal value. At the same time, (R)-Muskone is the main source of musk aroma, which can be well blended with various spices and has a long-lasting fragrance. It can be used as a fixative for high-end cosmetics. Due to the limited resources of natural musk, the market demand cannot be met, and artificially synthesizing (R)-muskone is the only way to solve the shortage of natural musk. [0003] In many synthetic routes of (R)-muscone, pentadecanedioic acid is used as raw material to obtain α-hydroxycyclic pentadecone throug...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/45C07C45/64C07C49/487
CPCC07C45/455C07C45/64C07C49/487
Inventor 高勇陈宏伟汪军方明章李媛媛汪慧霞肖玉麟
Owner FUJIAN NORMAL UNIV
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