Synthetic method for MDJ (Methyl Dihydrojasmonate)

A technique for the synthesis of methyl dihydrojasmonate, which is applied in the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, can solve problems such as ineffective effects, and achieve non-corrosiveness and reaction routes Simple, cheap ingredients

Inactive Publication Date: 2015-05-20
ANHUI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the bottleneck of the process route and raw material cost, industrial production has not been realized in China. In recent years, there have been many researches in China, and the effect is not very obvious. Therefore, it is important to seek a simpler process for this target compound. significance

Method used

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  • Synthetic method for MDJ (Methyl Dihydrojasmonate)
  • Synthetic method for MDJ (Methyl Dihydrojasmonate)
  • Synthetic method for MDJ (Methyl Dihydrojasmonate)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Into a three-necked flask equipped with a stirrer, a thermometer, and a dropping funnel, N 2 Protection, cool down to -78°C with dry ice and keep warm. After the temperature in the three-neck flask is stabilized at -78°C, start adding 18.5g of methyl acetate, then add 5ml of LDA with a syringe under stirring, and continue stirring to make lithium diisopropylamide Dissolve until the solution changes from colorless to light yellow, which is the generation of active methylene ions.

[0019] Change the ice-salt bath to adjust the temperature to -5°C, then add 38g of lactone dropwise to the dropping funnel, after 0.5h of dropwise addition, stir the reaction for 10min under the microwave power of 0.5KW to terminate the reaction, add dilute HCl to adjust pH to 6-7, then washed with saturated brine and left to separate layers, washed 3 times, collected the upper organic phase, evaporated the solvent and water under normal pressure, rectified under reduced pressure, and collecte...

Embodiment 2

[0021] Into a three-necked flask equipped with a stirrer, a thermometer, and a dropping funnel, N 2 Protection, cool down to -78°C with dry ice and keep warm. After the temperature in the three-necked flask is stabilized at -78°C, start adding 18.5g of methyl acetate, then add 10ml of LDA with a syringe under stirring, and continue stirring to make lithium diisopropylamide Dissolve until the solution changes from colorless to light yellow, which is the generation of active methylene ions.

[0022] Change the ice-salt bath to adjust the temperature to -5°C, then add 31.65g of internal ketone to the dropping funnel, after 0.5h of dropwise addition, stir the reaction for 10min under the microwave power of 0.5KW to terminate the reaction, add dilute HCl to adjust pH to 6-7, then wash with saturated brine and let stand to separate layers, wash 2-3 times, collect the upper organic phase, distill off the solvent and water under normal pressure, rectify under reduced pressure, and col...

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Abstract

The invention discloses a synthetic method for MDJ (Methyl Dihydrojasmonate), which comprises the following steps of removing protons from methyl acetate under the action of an alkaline reagent diisopropyl lithium amide to obtain active methylene ions, and carrying out Michael addition reaction on the active methylene ions and 2-amyl cyclopentenone under the action of microwaves to obtain the MDJ. The synthetic method provided by the invention has the advantages that the process path is simple, the raw materials for the reaction materials are cheap, and the pollution to the equipment and the environment is less, and meanwhile the yield of the product can reach 45%.

Description

technical field [0001] The invention relates to a method for synthesizing methyl dihydrojasmonate, belonging to the technical field of organic synthesis. Background technique [0002] Jasmine fragrance compounds have been studied for decades, but with the increasing demand for such compounds, the progress of their industrialization has been far from meeting the needs. Methyl Dihydrojasmonate (Methyl Dihydrojasmonate, MDJ) belongs to jasmone compound, is one of the important jasmine spices of artificial synthesis, has not found the related report that it exists in natural spices up to now, because its price is relatively cheap, It has a wide range of applications, so it is an important spice variety in the modern spice industry. Its appearance is colorless or light yellow transparent liquid, its chemical properties are relatively stable, it has the advantages of slow volatilization, long retention time of aroma, and no discoloration when used for fragrance. It is not only u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/716C07C67/347
CPCC07C67/347C07C69/716
Inventor 李广学彭飞马钊王安顺林伟黄珍丽施建林
Owner ANHUI UNIV OF SCI & TECH
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