A kind of preparation method of royal jelly acid

A technology of royal jelly acid and methyl propiolate, applied in carboxylate preparation, organic chemistry, etc., can solve the problems of high requirements for reaction conditions, high production costs, hindering the progress of the reaction, etc., and achieves easy industrial production and short reaction route , the effect of high total yield

Active Publication Date: 2022-03-08
JIAXING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation process of this process is relatively simple, but the oxidation uses PCC, the oxidant cannot be recycled and reused and there is heavy metal pollution
[0005] Chinese patent application CN101747181A uses 1,1-dialkoxy-6-hexylmagnesium halide as raw material to obtain royal jelly acid through a four-step reaction. The Grignard reagent used in this process is unstable and requires high reaction conditions, so it is also Not suitable for industrial production
The disadvantage of this method is that 8-hydroxyoctanal can form a hemiacetal structure in the molecule to hinder the next step of the reaction, and the catalyst Tempo used cannot be recycled.
Although the route of this method is relatively simple and has the characteristics of high total yield, it needs to be catalyzed by ionic liquid, and the production cost is relatively high.

Method used

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  • A kind of preparation method of royal jelly acid
  • A kind of preparation method of royal jelly acid
  • A kind of preparation method of royal jelly acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 8.4 g (0.1 mol) methyl propiolate, 30 mL dry tetrahydrofuran and 4.5 g (0.115 mol) sodium amide in a 100 mL single-necked bottle, stir the mixture at room temperature for about 15 minutes, then add 7-bromoheptanol dropwise 21.34 g (0.11 mol), continued to react for 3.0 h after 0.5 h of dropwise addition. After the reaction is complete, remove tetrahydrofuran in vacuo, dissolve the residue with dichloromethane, wash with water, separate the organic phase, anhydrous MgSO 4 After drying and filtering, the filtrate was evaporated to remove the solvent to obtain 19.2 g of compound II as a light yellow oily liquid, with a yield of 97%.

[0028] 1 HNMR (CDCl 3 ,δ(ppm),TMS):δ1.26-1.44(m,8H),1.49-1.58(m,2H),2.46(t,2H),3.62(t,2H),3.68(s,3H)4.08 (s,br,1H).

[0029] In a 100 mL single-necked flask at -40°C, 20 mL of liquid ammonia was passed, then 2.4 g (0.104 mol) of sodium metal was added, and 9.9 g (0.05 mol) of compound II prepared above was added, and the reaction was ...

Embodiment 2

[0034] Add 8.4 g (0.1 mol) methyl propiolate, 30 mL dry tetrahydrofuran and 4.1 g (0.105 mol) sodium amide into a 100 mL single-necked bottle, stir the mixture at room temperature for about 15 minutes, then add 7-bromoheptanol dropwise 20.37 g (0.105 mol), continued to react for 3.0 h after 0.5 h of dropwise addition. After the reaction is complete, remove tetrahydrofuran in vacuo, dissolve the residue with dichloromethane, wash with water, separate the organic phase, anhydrous MgSO 4 After drying and filtering, the filtrate was evaporated to remove the solvent to obtain 19.1 g of compound II as a light yellow oily liquid, with a yield of 96.5%.

[0035] In a 100 mL single-necked flask at -40°C, 20 mL of liquid ammonia was passed, then 2.5 g (0.108 mol) of sodium metal was added, and 9.9 g (0.05 mol) of compound II prepared above was added, and the reaction was stirred at low temperature for 2 h. After the reaction was completed, the liquid ammonia was removed by filtration, ...

Embodiment 3

[0038] Add 25.2 g (0.3 mol) methyl propiolate, 100 mL dry tetrahydrofuran and 12.3 g (0.315 mol) sodium amide in a 250 mL three-necked flask, stir the mixture at room temperature for about 30 minutes, then add 7-bromoheptanol dropwise 63.15 grams (0.326mol), after 1.0 hours of dropwise addition, the reaction was continued for 3.5 hours. After the reaction is complete, remove tetrahydrofuran in vacuo, dissolve the residue with dichloromethane, wash with water, separate the organic phase, anhydrous MgSO 4 After drying, filtering, and evaporating the filtrate to remove the solvent, 57.5 g of Compound II was obtained as a pale yellow oily liquid, with a yield of 96.8%.

[0039] 100 ml of liquid ammonia was passed into a 2050 mL single-necked flask at -40°C, then 10.3 g (0.445 mol) of sodium metal was added, and 40.2 g (0.203 mol) of compound II prepared above was added, and the reaction was stirred at low temperature for 2.5 h. After the reaction was completed, the liquid ammonia...

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PUM

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Abstract

The invention discloses a preparation method of royal jelly acid, which belongs to the field of chemical synthesis. It takes methyl propiolate and 7-bromoheptanol as starting materials, and in a solvent, under the action of strong base sodium amide, obtains methyl 10-hydroxy-2-decynoate; in liquid ammonia solvent, utilizes Sodium metal is trans-reduced to obtain (E)-10-hydroxy-2-decenoic acid methyl ester, then hydrolyzed under the action of alkali, and then acidified to obtain the target product royal jelly acid. The preparation method of royal jelly acid of the present invention has the characteristics of short route, simple operation and easy industrial production, and is a very economical and convenient method for synthesizing royal jelly acid.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and more specifically relates to a preparation method of royal jelly acid. Background technique [0002] Royal jelly acid is the main organic component of royal jelly, and its content is one of the main indicators to measure the quality of royal jelly. Its chemical name is (E)-10-hydroxy-2-decenoic acid, or 10-HDA for short. Because of its anti-bacterial, anti-cancer, anti-radiation and strong body and other physiological functions, it has attracted the attention of workers in the fields of chemistry, biology and medicine. At present, royal jelly and its products have become best-selling products in domestic and foreign markets. Although royal jelly acid can be extracted from royal jelly, the product prepared by synthetic method has high purity and quality is easier to guarantee. There are many synthetic routes published at home and abroad, but from a practical point of view, many routes are ei...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/02C07C59/42
Inventor 李梦宗乾收刘雪君汪露戴晶晶张雅晶郑滟男周宏伟包琳
Owner JIAXING UNIV
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