A kind of preparation method of α-hydroxy cyclopentadecanone

A technology of cyclopentadecanone and hydroxyl, which is applied in the field of preparation of α-hydroxy cyclopentadecanone by condensation of acetoin, which can solve problems such as instability of sodium potassium alloy and potential safety hazards, achieve simplified post-processing steps, and increase yield of acyloin condensation The effect of shortening the reaction time

Inactive Publication Date: 2018-10-26
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, sodium-potassium alloys are very unstable, and there are certain safety hazards in large-scale industrial use.
[0005] To sum up, there is still a lot of room for improvement in the yield of dipentadecanodiacidic acid ester condensation at present. If the yield of dual condensation can be further improved without increasing the cost and reducing potential safety hazards, then It is of great significance to the industrial production of muskone synthesis route using pentadecanedioic acid as raw material

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 1.15g (0.05mol) of sodium and 10mL of mineral oil into the conical flask, heat until the sodium melts, and slowly drop 10.35g of mercury into the conical flask with a dropping funnel. After the dropwise addition, stop heating and keep stirring to disperse the sodium amalgam into small pieces. The mineral oil was removed by filtration, and the filtered sodium amalgam (metal sodium content was 10wt%) was washed with petroleum ether and used directly for the next reaction.

[0032]Add 40mL of dry benzene and 11.5g of the above-mentioned newly prepared sodium amalgam into a dry three-necked flask equipped with a constant pressure dropping funnel, stirring, and a reflux condenser, protect with nitrogen, stir and slowly raise the temperature to 80°C, and then add the solution dropwise. 3.01g (0.01mol) of dimethyl pentadecanedioic acid in 10mL of benzene solution, after the dropwise addition, keep the reaction for 2 hours. After the reaction, the reaction solution was coo...

Embodiment 2

[0034] Add 2.76g (0.12mol) of sodium and 10mL of mineral oil into the conical flask, heat until the sodium melts, and slowly drop 15.64g of mercury into the conical flask with a dropping funnel. After the dropwise addition, stop heating and keep stirring to disperse the sodium amalgam into small pieces. The mineral oil was removed by filtration, and the filtered sodium amalgam (metal sodium content was 15wt%) was washed with petroleum ether and used directly for the next reaction.

[0035] Add 40mL of dry xylene and 18.4g of the above-mentioned newly prepared sodium amalgam into a dry three-necked flask with a constant pressure dropping funnel, stirring, and a reflux condenser, protect with nitrogen, stir and slowly heat up to 140°C, then dropwise add Dissolve 3.01g (0.01mol) of dimethyl pentadecanedioic acid in 10mL of xylene solution, after the dropwise addition, keep the reaction for 6 hours. After the reaction, the reaction solution was cooled to room temperature, and fil...

Embodiment 3

[0037] Add 0.46g (0.02mol) of sodium and 10mL of mineral oil into the conical flask, heat until the sodium melts, and slowly drop 22.54g of mercury into the conical flask with a dropping funnel. After the dropwise addition, stop heating and keep stirring to disperse the sodium amalgam into small pieces. The mineral oil was removed by filtration, and the filtered sodium amalgam (metal sodium content was 2wt%) was washed with petroleum ether and used directly for the next reaction.

[0038] Add 40mL of dry toluene and 23g of the above-mentioned newly prepared sodium amalgam into a dry three-necked flask with a constant pressure dropping funnel, stirring, and a reflux condenser, protect with nitrogen, stir and slowly heat up to 120°C, and then dropwise add the dissolved 3.01g (0.01mol) 10mL toluene solution of dimethyl pentadecanedioate, after the dropwise addition, keep the reaction for 4 hours. After the reaction, the reaction solution was cooled to room temperature, and filte...

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PUM

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Abstract

The invention discloses a preparation method for alpha-hydroxycyclopentadecanone. According to the preparation method, the alpha-hydroxycyclopentadecanone is prepared through acyloin condensation by taking pentadecanedioic diester as a raw material and taking sodium amalgam as a reducing agent. The preparation method for the alpha-hydroxycyclopentadecanone has the characteristics that the using amount of sodium is small, post-processing steps are simple, the reaction time is short, the acyloin condensation yield is high, and the like. The reaction conditions of the preparation method are easy to control; the production cost is low; cyclization products are convenient to separate; the industrial production is easy to realize.

Description

technical field [0001] The present invention relates to a preparation method of α-hydroxycyclopentadecone, specifically a method for preparing α-hydroxycyclopentadecone by using pentadecanedioic acid diester as a raw material and sodium amalgam as a reducing agent through azoin condensation The keto approach. Background technique [0002] Muscone is the main functional component of natural musk, and its chemical name is (R)-3-methylcyclopentadecanone. Muscone has some important pharmacological effects of natural musk, and can treat a variety of diseases. At the same time, muscone is the main source of musk aroma. It can be well blended with various spices and has a long-lasting fragrance. It can be used as a fixative for high-end cosmetics . Natural musk resources are becoming scarce day by day, and the demand for musk can be basically replaced by artificially synthesizing muskone, which is the main method to solve the current shortage of musk. [0003] At present, the me...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/45C07C49/487
CPCC07C45/455C07C49/487
Inventor 高勇张晓伟汪军陈宏伟付妹方明章肖玉麟杨晓航
Owner FUJIAN NORMAL UNIV
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