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Method for synthesizing methyleugenol

A technology for synthesizing eugenol methyl ether, which is applied in chemical instruments and methods, preparation of ether, preparation of ether by ester reaction, etc., can solve problems such as high-purity separation difficulties, environmental hazards, and dimethyl sulfate is highly toxic, and achieves Simple purification, reduced environmental pollution, and less toxic effects on the human body

Active Publication Date: 2018-04-17
KUNSHAN YAXIANG SPICEL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the method is simple and the yield is high, dimethyl sulfate is highly toxic and highly corrosive to the skin and the reaction device. It will cause unsafe factors to the human body during use and cause great harm to the environment.
At the same time, due to the potassium sulfate produced, it brings great difficulties to the high-purity separation of the product

Method used

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  • Method for synthesizing methyleugenol
  • Method for synthesizing methyleugenol

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Example 1. Dissolve 144.5g (1mol, 1eq) of 4-chloroquinone in 500ml toluene and put it into a reaction flask, then add 5.6g KOH, 5g K ion-type molecular sieve and 180g dimethyl carbonate, and open 1g TBAB Stir and heat to 70-80°C, react for 8-12 hours, TLC (silica gel plate chromatography separation, commonly known as climbing plate) to confirm the completion of the reaction, cool, filter, distill, add 10% hydrochloric acid to adjust the pH to 7, and then use n-hexane Extract, dry and distill to obtain 162g of 4-chloroquinone methyl ether with a purity of 95%.

[0020] The obtained 162g of 4-chloroquinone methyl ether was dissolved in 300ml of anhydrous ether for subsequent use. Put 24g of Mg pin into the reaction bottle, add 300ml of anhydrous ether and 2 iodine, start stirring, nitrogen protection, drop 20ml of 4-chloroquinone methyl ether, and then add 3~5ml of dibromoethane . After the reaction was initiated, the remaining anhydrous diethyl ether solution of 4-chlo...

Embodiment 2

[0022] Example 2. Dissolve 144.5g (1mol, 1eq) of 4-chloroquinone in 500ml of toluene and put it into a reaction flask, then add 10% aqueous solution containing 28g of KOH and 180g of dimethyl carbonate, 1g of TBAB is turned on, stirred and heated to reflux , reacted for 8 to 12 hours, after confirming the completion of the reaction, cooled, adjusted to PH=7 with 10% hydrochloric acid, then extracted with n-hexane, dried and distilled to obtain 138g of 4-chloroquinone methyl ether with a purity of 97%.

[0023] The obtained 138g of 4-chloroquinone methyl ether was dissolved in 300ml of anhydrous ether for subsequent use. Put 20g of Mg pin into the reaction bottle, add 300ml of anhydrous ether and 2 grains of iodine, start stirring, nitrogen protection, drop 20ml of 4-chloroquinone methyl ether, and then add 3~5ml of dibromoethane . After the reaction was initiated, the remaining anhydrous diethyl ether solution of 4-chloroquinone methyl ether was added dropwise. After the reac...

Embodiment 3

[0025] Example 3. Dissolve 2kg of 4-chloroquinone in 10L of toluene and put it into a reaction kettle, then add 553g of NaOH, 50g of K ion-type molecular sieve and 2.5Kg of dimethyl carbonate, and start stirring with 50g of TBAB and heat to 70-80 ℃, reacted for 8 to 12 hours, after confirming that the reaction was complete, cooled, filtered, and distilled, adjusted to PH=7 with 15% hydrochloric acid, then extracted with n-hexane, dried, and distilled to obtain 2.26Kg 4-chloroquinone methyl ether, 96% purity.

[0026] The obtained 2.26Kg of 4-chloroquinone methyl ether was dissolved in 5L of n-hexane for later use. Put 320g of Mg pin into the reaction bottle, add 5L of anhydrous ether and 2 grains of iodine, start stirring, nitrogen protection, drop 300ml of 4-chloroquinone methyl ether, and then add 10-20ml of dibromoethane . After the reaction was initiated, the remaining anhydrous diethyl ether solution of 4-chloroquinone methyl ether was added dropwise. After the reaction...

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Abstract

The invention discloses a method for synthesizing methyleugenol. The method is characterized by comprising the following steps: reacting 4-halo-benzenediol and methyl to synthesize 4-halo-benzenediolmethyl ether; reacting the 4-halo-benzenediol methyl ether and magnesium to produce magnesium halide 4-benzenediol methyl ether; and reacting the magnesium halide 4-benzenediol methyl ether and 3-halo-1-propyl olefin to produce methyleugenol. According to the method for synthesizing methyleugenol, provided by the invention, the methylation reaction is carried out first, and a Grignard reagent and3-halo-1-propyl olefin react to obtain the methyleugenol. The overall yield reaches 80% or higher, the purification is simple, and non-toxic dimethyl carbonate or alkyl halide is used in the process flow, so that the process is small in human toxic and side effects, and environmental pollution is reduced.

Description

technical field [0001] The invention relates to the synthetic field of flavoring agents, in particular to a synthetic method of clove methyl ether. Background technique [0002] Eugenol methyl ether is one of the important ingredients in the preparation of fragrances. It is used in the preparation of carnation, oriental, spicy and woody fragrances. It can be widely used in carnation, rose, lilac, ylang-ylang and other floral fragrances. The fixative can be formulated according to different styles, and it can also be used as a food flavor in tobacco and chocolate. [0003] The eugenol methyl ether in the prior art is prepared by methylating eugenol. Specifically, eugenol is added into potassium hydroxide aqueous solution, then dimethyl sulfate is added, and then the oil layer is distilled to obtain eugenol methyl ether. Although the method is simple and has a high yield, dimethyl sulfate is highly toxic and highly corrosive to skin and reaction devices, causing unsafe facto...

Claims

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Application Information

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IPC IPC(8): C07C41/16C07C43/225C07C41/30C07C43/215
CPCC07C41/16C07C41/30C07C43/225C07C43/215
Inventor 周军学陈清
Owner KUNSHAN YAXIANG SPICEL CO LTD
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