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Method for synthesizing beta-myrcene through intramolecular decarboxylation allyl substitution reaction

A technology of allyl substitution and carboxyallyl, applied in the field of fine chemicals, can solve the problems of no commercial value, low energy consumption, etc.

Active Publication Date: 2022-07-29
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
At present, the route of artificial synthesis of 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 intramolecular decarboxylation allyl substitution reaction
  • Method for synthesizing beta-myrcene through intramolecular decarboxylation allyl substitution reaction
  • Method for synthesizing beta-myrcene through intramolecular decarboxylation allyl substitution reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment i

[0055] Synthesis of compound I.

[0056]

[0057] In a flask, add 3-methylene-4-enevaleric acid (1 mol), 3-methyl-2-buten-1-ol (1 mol) and 200 ml of dichloromethane, stir mechanically, and let the system cool down to After 0 °C, dicyclohexylcarbodiimide (DCC) (1.1 mol) and 4-dimethylaminopyridine (DMAP) (0.2 mol) were added to the system, then the temperature was raised to room temperature, and the reaction was continued to stir for 12 h to stop the reaction. The solid was filtered off with celite, and the filtrate was washed with 5% HCl, saturated NaHCO successively 3 It was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed in vacuo. The residue was separated by silica gel column chromatography to obtain product I (yield 94%). 1 H NMR (400MHz, C 6 D 6 ): δ1.69(s, 3H), 1.78(s, 3H), 3.58(s, 2H), 4.48(d, 2H), 4.79–5.01(m, 2H), 5.10–5.20(m, 2H), 5.35 (m, 1H), 6.24 (m, 1H).

[0058] Example ii

[0059] Synthesis of compound I....

Embodiment iv

[0065] Synthesis of compound I.

[0066] In a flask, add 3-methylene-4-enevaleric acid (1 mol), 3-methyl-2-buten-1-ol (1.2 mol) and 200 ml of dichloromethane, stir mechanically, and wait for the system to cool After reaching 0 °C, dicyclohexylcarbodiimide (DCC) (1.1 mol) and 4-dimethylaminopyridine (DMAP) (0.2 mol) were added to the system, then the temperature was raised to room temperature, and the reaction was continued for 1 h to stop the reaction. , the solid was filtered off with celite, and the filtrate was successively washed with 5% HCl, saturated NaHCO 3 It was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was removed in vacuo, and the residue was isolated by silica gel column chromatography to obtain product I (yield 83%).

Embodiment v

[0068] Synthesis of compound I.

[0069] In a flask, add 3-methylene-4-enevaleric acid (1 mol), 3-methyl-2-buten-1-ol (1.2 mol) and 200 ml of dichloromethane, stir mechanically, and wait for the system to cool After reaching -10°C, add dicyclohexylcarbodiimide (DCC) (1.1mol) and 4-dimethylaminopyridine (DMAP) (0.2mol) to the system, then warm to room temperature, continue to stir the reaction for 12h, stop After the reaction, the solid was filtered off with celite, and the filtrate was successively washed with 5% HCl, saturated NaHCO 3 It was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was removed in vacuo, and the residue was isolated by silica gel column chromatography to obtain product I (yield 99%).

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Abstract

The invention provides a method for synthesizing beta-myrcene through an intramolecular decarboxylation allyl substitution reaction. The method comprises the following steps: by taking a compound I as an initial raw material, generating a nucleophilic reagent in situ through intramolecular decarboxylation under the action of a catalyst formed by metal salt and a new ligand, and then carrying out allyl substitution reaction to synthesize the beta-myrcene. The invention provides a novel method for synthesizing beta-myrcene, which has the advantages of low reaction temperature, few side reactions, high selectivity and high yield.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a method for synthesizing β-myrcene through intramolecular decarboxylation allyl substitution reaction. Background technique [0002] β-Myrcene, also known as mercene, 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. It can synthesize menthol, citral, and citronellol. , geraniol, nerol, linalool, citrus aldehyde, new lily aldehyde, cycloalkene nitrile, syringol, syring ether, sanalactone and ambergris compounds and other compounds. [0003] The sources of β-myrcene mainly include natural extraction and artificial synthesis. Natural β-myrcene can be extracted from the essential oils of bay leaves, verbena, geranium and other plants; but the content of β-myrcene in natural essential oils is very small, which is far from meeting the requirements ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/207C07C11/21
CPCC07C1/2078C07C2531/24C07C11/21
Inventor 张德旸张永振陈长生王坤姜鹏刘连才黎源
Owner WANHUA CHEM GRP CO LTD
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