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Method for synthesizing beta-myrcene through intermolecular nucleophilic addition reaction

An addition reaction and intermolecular technology, applied in the direction of condensation between hydrocarbons and non-hydrocarbons, organic chemistry, etc., can solve problems such as no commercial value, low energy consumption, etc.

Pending Publication Date: 2022-04-12
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

CN111454114A has reported the synthesis of lauryl alcohol by geraniol, the method does not use metal catalysts and additives, the reaction is mild, but the use of geraniol with higher economic value to synthesize β-myrcene has no commercial value in industry
The current route of artificially synthesizing β-myrcene has many shortcomings, so it is of great significance to develop a new route with low energy consumption, high selectivity and mild conditions to synthesize β-myrcene

Method used

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  • Method for synthesizing beta-myrcene through intermolecular nucleophilic addition reaction
  • Method for synthesizing beta-myrcene through intermolecular nucleophilic addition reaction
  • Method for synthesizing beta-myrcene through intermolecular nucleophilic addition reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment i

[0049] Compound I-1 was synthesized.

[0050]

[0051] In the flask, add trimethyl orthoacetate (1mol), 2-methyl-3-buten-2-ol (1mol) and propionic acid (0.2mol), then heat the reaction system to 125°C and continue to stir the reaction 12h, stop the reaction. followed by water, saturated NaHCO 3 Wash with saturated brine, dry over anhydrous sodium sulfate, and carry out vacuum distillation under the conditions of 30hPa and 70°C to obtain compound I (yield 98%). The characterization results are: 1 H NMR (400MHz, CDCl 3 ):δ1.61(s,3H),1.67(s,3H),2.30–2.35(m,4H),3.68(s,3H),5.08–5.10(m,1H); 13 CNMR (100MHz, CDCl 3 ): δ17.7, 23.4, 25.5, 34.1, 51.4, 122.3, 133.1, 173.5.

[0052] Example II

[0053] Compound 1-2 was synthesized.

[0054]

[0055] In the flask, add triethyl orthoacetate (1mol), 2-methyl-3-buten-2-ol (1mol) and propionic acid (0.2mol), then heat the reaction system to 125°C and continue to stir the reaction 12h, stop the reaction. followed by water, sat...

Embodiment 1

[0057] Synthesis of the compound β-myrcene.

[0058] metal salt AuNTf 2 After complexing with ligand II-1, it is used as a catalyst to catalyze the reaction to prepare β-myrcene.

[0059] Under the protection of nitrogen, the metal salt AuNTf was added into the three-necked flask 2 (0.03mol, 3mol%) and ligand II-1 (0.033mol, 3.3mol%) were added to 200ml of dichloromethane, and stirred at room temperature for 1h. Then the above catalyst solution, triethylamine (2.5mol, 2.5equiv) and compound I-1 (1mol, 1equiv) in Example i were added to the pressure-resistant reactor, and vinylacetylene (1.2mol, 1.2equiv) ), and then the above system was heated to 50° C. for 12 h. Stop the reaction, cool to room temperature, discharge the remaining vinyl acetylene in the system, then raise the temperature to 115°C to continue the reaction for 6h, stop the reaction, open the reaction kettle, the reaction liquid is analyzed by the gas phase internal standard method, the conversion rate is 96%,...

Embodiment 2

[0061] Synthesis of the compound β-myrcene.

[0062] metal salt AuNTf 2 After complexing with ligand II-1, it is used as a catalyst to catalyze the reaction to prepare β-myrcene.

[0063] Under the protection of nitrogen, the metal salt AuNTf was added into the three-necked flask 2 (0.03mol, 3mol%) and ligand II-1 (0.033mol, 3.3mol%) were added to 200ml of dichloromethane, and stirred at room temperature for 1h. Then the above-mentioned catalyst solution, triethylamine (2.5mol, 2.5equiv) and compound II-2 (1mol, 1equiv) in Example i were added to the pressure-resistant reactor, and vinylacetylene (1.2mol, 1.2equiv) was passed into ), and then the above system was heated to 50° C. for 12 h. Stop the reaction, cool to room temperature, drain the remaining vinyl acetylene in the system, then raise the temperature to 115°C to continue the reaction for 6h, stop the reaction, open the reaction kettle, the reaction liquid is analyzed by the gas phase internal standard method, the ...

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Abstract

The invention provides a method for synthesizing beta-myrcene through an intermolecular nucleophilic addition reaction. According to the method, a compound I and vinyl acetylene are taken as starting raw materials, an alkali additive is added, and the beta-myrcene is synthesized through an intermolecular nucleophilic addition reaction under the action of a catalyst formed by metal salt and a ligand. The novel method for synthesizing the beta-myrcene is provided, the raw materials are cheap and easy to obtain, the reaction temperature is low, the selectivity is high, the yield is high, and the operation is simple.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and specifically relates to a method for synthesizing β-myrcene through intermolecular nucleophilic addition. Background technique [0002] β-Myrcene, also known as myrcene, has a pleasant sweet balsamic smell and can be used directly as a fragrance. It is one of the most important raw materials and intermediates in the fragrance industry, and can also be used to synthesize other fragrances. The sources of β-myrcene mainly include natural extraction and artificial synthesis. At present, artificial synthesis is the main source of β-myrcene, which is mainly synthesized by pyrolysis of β-pinene. [0003] Patent CN107602322A reports a process and production device for producing β-myrcene through thermal cracking of β-pinene. The author processes the raw material β-pinene into micron-sized droplets by ultrasonic atomization, thereby reducing the concentration of β-pinene The temperature at wh...

Claims

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Application Information

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IPC IPC(8): C07C2/86C07C11/21
Inventor 张德旸姜鹏刘连才蔺海政张稳张永振黎源
Owner WANHUA CHEM GRP CO LTD
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