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Preparation method of abietic acid derivative

A technology of abietic acid and derivatives, which is applied in the field of preparation of abietic acid derivatives, can solve the problems of low product yield, low yield, and easy formation of polymers, and achieve low reaction conditions, high yield, and product purity. Improved effect

Active Publication Date: 2017-03-15
XIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield of the whole process route is very low, especially in the reduction reaction step of Huang Minglong, because the reaction temperature is too high, >200°C, it is easy to form polymers, the product yield is very low and the repeatability is not good

Method used

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  • Preparation method of abietic acid derivative
  • Preparation method of abietic acid derivative
  • Preparation method of abietic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation method of rosin acid derivatives includes the following steps:

[0030] (1) Dissolve abietic acid 1 in a solvent, add alkali under stirring at room temperature, stir for fifteen minutes, add iodoethane, heat up to 60°C and react for 24 hours, extract, wash, dry, and concentrate to obtain Intermediate 2;

[0031] (2) Dissolve Intermediate 2 in a solvent, add lithium tetrahydroaluminum in an ice bath, stir for 4 hours at room temperature, adjust the pH to 6 with dilute hydrochloric acid, filter and spin off the filtrate, extract, wash, dry, and concentrate to obtain Intermediate 3;

[0032] (3) Dissolve Intermediate 3 in a solvent, add p-toluenesulfonyl chloride with stirring in an ice bath, the molar ratio of Intermediate 3: p-toluenesulfonyl chloride is 1:3, stir and react at room temperature for 6 hours, filter, extract, and wash , Dried and concentrated to obtain intermediate 4;

[0033] (4) Intermediate 4 is dissolved in the solvent, added to NaI and Zn unde...

Embodiment 2

[0038] The preparation method of rosin acid derivatives includes the following steps:

[0039] (1) Dissolve abietic acid 1 in a solvent, add alkali under stirring at room temperature, stir for fifteen minutes, add bromoethane, heat up to 60°C for 26 hours, extract, wash, dry, and concentrate to obtain Intermediate 2;

[0040] (2) Dissolve Intermediate 2 in a solvent, add lithium tetrahydroaluminum in an ice bath, stir at room temperature for 3 hours, adjust the pH to 6 with dilute hydrochloric acid, filter and spin off the filtrate, extract, wash, dry, and concentrate to obtain Intermediate 3;

[0041] (3) Dissolve Intermediate 3 in a solvent, add p-toluenesulfonyl chloride with stirring in an ice bath, the molar ratio of Intermediate 3: p-toluenesulfonyl chloride is 1:5, stir and react at room temperature for 6 hours, filter, extract, and wash , Dried and concentrated to obtain intermediate 4;

[0042] (4) Intermediate 4 is dissolved in a solvent, added to NaI and Zn under stirring ...

Embodiment 3

[0047] The preparation method of rosin acid derivatives includes the following steps:

[0048] (1) Dissolve abietic acid 1 in a solvent, add alkali under stirring at room temperature, stir for 15 minutes, add chloroethane, heat up to 60°C for 28 hours, extract, wash, dry, and concentrate to obtain Intermediate 2;

[0049] (2) Dissolve Intermediate 2 in a solvent, add lithium tetrahydroaluminum under an ice bath, ， Stir the reaction at room temperature for 4 hours, adjust the pH to 6 with dilute hydrochloric acid, filter and spin off the filtrate, extract, wash, dry, and concentrate to obtain Intermediate 3;

[0050] (3) Dissolve Intermediate 3 in a solvent, add p-toluenesulfonyl chloride with stirring in an ice bath, the molar ratio of Intermediate 3: p-toluenesulfonyl chloride is 1:6, stir and react at room temperature for 6 hours, filter, extract, and wash , Dried and concentrated to obtain intermediate 4;

[0051] (4) Intermediate 4 is dissolved in a solvent, added to NaI and Zn un...

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Abstract

The invention belongs to the technical field of chemical pharmacy, and particularly discloses a preparation method for an abietic acid derivative. Abietic acid 1 is dissolved in solvent, alkali is added, halogenated hydrocarbon is added, and then an intermediate 2 is obtained; the intermediate 2 is dissolved in solvent, lithium aluminum hydride is added, the pH is regulated to 6 through diluted hydrochloric acid, and then an intermediate 3 is obtained; the intermediate 3 is dissolved in solvent, paratoluensulfonyl chloride is added, and then an intermediate 4 is obtained; the intermediate 4 is dissolved in solvent, NaI and Zn are added, and then an intermediate 5 is obtained; the intermediate 5 is dissolved in solvent, hydrogen bromide is added, washing is performed through frozen glacial acetic acid, and then an intermediate 6 is obtained; the intermediate 6 is dissolved in solvent, alkali is added, diluted hydrochloric acid is added to regulate the PH to 2-3, and then an intermediate 7 is obtained; the intermediate 7 is dissolved in solvent, selenium dioxide is added, and a product 8 is obtained. According to the preparation method of the abietic acid derivative, the yield is high; particularly, Huang-Minlon reduction reaction needing high temperature is avoided, so that the requirement for reaction conditions is low; in addition, the product purity is greatly improved.

Description

Technical field [0001] The invention belongs to the technical field of chemical pharmacy, and is specifically a preparation method of abietic acid derivatives. Background technique [0002] Rosin acid is used as a traditional Chinese medicine because it has good biological activity. Many of them are agricultural chemicals, and their derivatives are mostly used in the synthesis of medicine. At present, the synthesis process of rosin acid derivatives reported in domestic and foreign literature is to first esterify the carboxyl group of rosin acid, then add, eliminate, and oxidize the conjugated double bond to build an aromatic ring. Finally, the carboxyl group is reduced by lithium aluminum hydride. Oxidation, Huang Minglong reduction, and finally C-4 with geminal dimethyl rosin acid derivatives. The yield of the whole process route is very low, especially in the step of Huang Minglong reduction reaction. Because the reaction temperature is too high, >200℃, it is easy to form p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/48C07C33/34
CPCC07C1/30C07C1/322C07C17/08C07C29/147C07C29/48C07C67/11C07C303/28C07C2603/26C07C33/34C07C13/60C07C23/44C07C309/73C07C33/14C07C69/753
Inventor 钱珊何彦颖陈泉龙张曼王伟袁陈
Owner XIHUA UNIV