Synthesis process for novel heliotropin monoester

A technology of jasmonal monoester and synthesis process, which is applied in the direction of organic chemistry, can solve the problems of high loss of reactants, poor selectivity, long reaction time, etc., and achieve the effect of reducing synthesis time, reducing operation steps and improving technical solutions

Inactive Publication Date: 2015-05-27
成都建中香料香精有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Neojasmonal monoester can theoretically be used as one of the intermediates for the total synthesis of jasmonal, but the main synthetic route of the existing jasmonal is to use jasmonal as a raw material, and undergo an aldol condensation reaction with propionaldehyde to obtain The final catalytic reduction of piperonyl propionaldehyde is to obtain the crude product of Xinyangjasmonal, and then the finished product can be obtained by distillation under reduced pressure. At present, in this respect, the yield is generally improved by adjusting the catalytic system, but the yield and purity are gener...

Method used

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  • Synthesis process for novel heliotropin monoester
  • Synthesis process for novel heliotropin monoester
  • Synthesis process for novel heliotropin monoester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] A kind of synthetic technique of new ocean jasmonal monoester, comprises the following steps:

[0032] (1) Esterification reaction: under certain temperature conditions, add acetic anhydride to methacrolein, after the reaction is complete, an esterification intermediate is obtained;

[0033] (2) Alkylation reaction: under certain temperature conditions, piperonyl cyclocyclene is added to the esterification intermediate in step (1), and the reaction is completely separated after alkali washing and water washing to separate the new jasmonal monoester.

[0034] Wherein, the catalyst used in the step (1) esterification reaction and the step (2) alkylation reaction is boron trifluoride diethyl ether, and the catalyst consumption in the step (1) esterification reaction adopts a catalytic equivalent, expressed as methacrolein The amount of the catalyst is 0.001-0.05 in terms of the amount of the substance, and the amount of the catalyst in the alkylation reaction in step (2) i...

Embodiment 2

[0043] Adopt the synthetic technique of embodiment one to synthesize new jasmonal monoester, concrete reaction condition is: the temperature of step (1) esterification reaction is-10-5 ℃; Step (2) in the alkylation reaction, piperonyl ring and esterification The molar ratio of the intermediate is 4-6, and the alkylation reaction temperature is 0-5° C. According to the difference in the molar ratio of methacrolein and acetic anhydride in step (1), 5 comparative examples are set and numbered respectively, respectively The molar ratio of methacrolein to acetic anhydride: 0.5-1(1), 1-1.1(2), 1.1-1.25(3), 1.25-1.5(4), 1.5-2(5).

[0044] The resulting product after the reaction is sampled respectively and detected by LC / MS to obtain the purity and yield of the esterification intermediate in step (1) and the purity and yield of step (2) new jasmonal monoester, and record the reaction time, Experimental data as table 2 .

[0045] Table 2 Each product detection data result of embo...

Embodiment 3

[0049] Adopt the synthesis process of Example 1 to synthesize new jasmonal monoester, the specific reaction conditions are: the temperature of step (1) esterification reaction is -10-5 ℃, the molar ratio of methacrolein and acetic anhydride is 1.1-1.25 ; In the step (2) alkylation reaction, the mol ratio of piperonyl ring and the esterification intermediate is 4-6, according to the difference of the alkylation temperature in the step (2) 4 comparative examples are set and numbered respectively, are respectively alkyl Melting temperature: -10—0°C (Ⅰ), 0—5°C (II), 5—20°C (Ⅲ), 20—40°C (Ⅳ).

[0050] The resulting product after the reaction is sampled respectively and detected by LC / MS to obtain the purity and yield of the esterification intermediate in step (1) and the purity and yield of step (2) new jasmonal monoester, and record the reaction time, Experimental data as table 3 .

[0051] table 3 Each product detection data result of embodiment three

[0052]

[0053] As...

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Abstract

The invention discloses a synthesis process for novel heliotropin monoester, which comprises the technical steps of esterification reaction and alkylation reaction. At a temperature between minus 30 DEG C and 30 DEG C, acetic anhydride is added into methylacrolein, an esterification intermediate is obtained after full reaction, the mole ratio of the methylacrolein and the acetic anhydride is 0.5-2, then at a temperature between minus 10 DEG C and 40 DEG C, enzodioxole is added into the esterification intermediate, and the novel heliotropin monoester is separated through alkali washing and water rinsing after full reaction. The steps of the process disclosed by the application can be carried out in the same reaction still, and through changing the temperature, the material ratio, and the catalytic system, the novel heliotropin monoester can be synthesized with a yield higher than 90%; the condition of the process method is mild and controllable, the reaction time is short, the operation is simple, the side products are fewer, and the synthesized novel heliotropin monoester is high in purity.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a synthesis process of Xinyang jasmonal monoester. Background technique [0002] Xinyang jasmonal monoester, chemical name 1-acetoxy-2-methyl-3-(3,4-methylenedioxyphenyl)-1-propene, is a light yellow solid with a melting point of 55— 56°C, its structural formula is as follows: [0003] [0004] Neojasmonal monoester can theoretically be used as one of the intermediates for the total synthesis of jasmonal, but the main synthetic route of the existing jasmonal is to use jasmonal as a raw material, and undergo an aldol condensation reaction with propionaldehyde to obtain The final catalytic reduction of piperonyl propionaldehyde is to obtain the crude product of Xinyangjasmonal, and then the finished product can be obtained by distillation under reduced pressure. At present, in this respect, the yield is generally improved by adjusting the catalytic system, but the yield and pur...

Claims

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Application Information

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IPC IPC(8): C07D317/54
CPCC07D317/54
Inventor 黄凤李永红李良龙曾林久吴高强马妙玲贺显伟廖英陈军李波黄宗凉罗兵
Owner 成都建中香料香精有限公司
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