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Synthetic method for beta-isophorone trimethyl silane enol ether and its use in synthetic large column trienic ketone

A technology of isophorone trimethylsilyl enol ether and isophorone trimethylsilyl ether, which is applied in the synthesis field of beta-isophorone trimethylsilyl enol ether, can solve production difficulties, Problems such as long reaction steps and high toxicity of hexamethylphosphoric triamide

Active Publication Date: 2005-05-18
APPLE FLAVOR & FRAGRANCE GRP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The disadvantage of the above-mentioned method is that the synthesis of β-isophorone trimethylsilane enol ether firstly uses methylmagnesium bromide Grignard reagent to react with isophorone, because the Grignard reagent is not particularly stable and needs to be separately It is more cumbersome to prepare and use it now, and it is more cumbersome to operate, and a large amount of ether is dangerous as a solvent, and hexamethylphosphoric triamide (HMPT) is very toxic, and the temperature requirement for the reaction is low (-20 ° C). The time is very long to 24 hours, all this makes this method can only be limited to the laboratory, and is difficult to carry out large-scale production
[0010] However, in the synthesis of macrotrienone by using β-isophorone trimethylsilane enol ether, the synthesis reaction temperature of 3-oxoα-turkyl alcohol is quite low at -60°C, and a large amount of moldy and large Dichloromethane with a low boiling point is very difficult for us to realize large-scale production in our country; in the last step, we must first react pyridine with methylsulfonyl chloride to obtain methylsulfonate, and then remove methylsulfonate in toluene to obtain large Column trienone, long reaction steps, cumbersome operation

Method used

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  • Synthetic method for beta-isophorone trimethyl silane enol ether and its use in synthetic large column trienic ketone
  • Synthetic method for beta-isophorone trimethyl silane enol ether and its use in synthetic large column trienic ketone
  • Synthetic method for beta-isophorone trimethyl silane enol ether and its use in synthetic large column trienic ketone

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Embodiment 1

[0020] Synthesis of β-isophorone trimethylsilane enol ether: add 400mlDMF and 320g (3.2mol) triethylamine in a 2000ml three-neck flask equipped with stirring, condenser, thermometer and dropping funnel, add under stirring 300g NaI (2mol) and 276g (2mol) of β-isophorone were cooled with ice water, t = about 10°C, 290g (2.7mol) of trimethylchlorosilane was added dropwise, and the temperature was controlled at about 25°C. After the drop was completed, the reaction was stirred at about 25°C for 6 hours, and a large amount of precipitates appeared at the bottom. Filtrate, pour the filtrate into 800g ice water, separate the water layer and extract it with 250ml*2 petroleum ether, combine the petroleum ether liquid and the oil layer, wash with dilute HCl, then wash with brine until neutral, add 10g of anhydrous magnesium sulfate to dry, recover After petroleum ether, distill under reduced pressure, collect the fraction at 68-70°C / 3-4mmHg, and obtain 321g of product, the content is ab...

Embodiment 2

[0022] Application of β-isophorone trimethylsilane enol ether in the synthesis of large column trienone: first synthesize β-isophorone trimethylsilane enol ether with the method and steps of the above-mentioned embodiment one, and then In the 2000ml three-neck flask that is equipped with stirring, condenser, thermometer and dropping funnel, add 321g (90%, 1.37mol) above-mentioned synthetic β-isophorone trimethylsilane enol ether, 500ml anhydrous toluene and 115g (99% 1.64mol) crotonaldehyde, cooled to -25 ° C, began to drop BF 3 .Et 2 O194g (1.37mol), the temperature has risen, and the drop is completed in about 1 hour, the temperature is about -20°C, and the reaction is about -20°C for 8 hours after the drop is completed. Then slowly add 126g Na from the dropping funnel 2 CO 3 Mix the solution with 600g water, stir for 10 minutes, pour it into a 2000ml separatory funnel, separate the water layer, wash the oil layer with water until neutral, recover the toluene, and fractio...

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Abstract

The synthesis process of beta-isophorone trimethyl silane enol ether includes the reaction between beta-isophorone and trimethyl chlorosilane under the catalysis of sodium iodide to obtain beta-isophorone trimethyl silane enol ether. The said beta-isophorone trimethyl silane enol ether is made to produce Aldol react with crotonaldehyde, and the product is heated to dewater to produce large column trienic ketone. The present invention has the advantages of simple operation and high yield, and is suitable for industrial production. The synthesized large column trienic ketone is used in cigarette essence and has excellent effect.

Description

technical field [0001] The present invention relates to a synthesis method of β-isophorone trimethylsilane enol ether, and also relates to the application of this compound in synthesizing the important tobacco spice macrotrienone. Background technique [0002] As one of the C-9 compounds in carotenoid degradation products, isophorone has the same parent structure as other carotenoid degradation products C-13 compounds, and this type of compound is used in synthetic flavors (especially in cigarettes) The status of spices) is very important, such as: ionone, turkone, turkenone, large column trienone, 3-oxo ionone, 3-oxoionol, theaspirane, theaspirinone, dihydro Actinolactone, etc., and isophorone, as an important chemical raw material and solvent, can be obtained by condensation and cyclization of acetone very conveniently, and the price is very low. Therefore, how to synthesize high value-added fragrance products from cheap and good-quality isophorone has always been the dir...

Claims

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Application Information

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IPC IPC(8): C07F7/18
Inventor 陈恩治
Owner APPLE FLAVOR & FRAGRANCE GRP
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