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Synthesis process of 10-HDA (10-hydroxy-2-decenoic acid)

A 10-HDA and 1.10-HDA technology, applied in the field of new synthesis technology, can solve the problems of low yield, high cost, harsh reaction conditions, etc., and achieve the effect of high yield, simple method and improved utilization rate

Inactive Publication Date: 2012-07-25
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to overcome the problems of high cost, harsh reaction conditions and low yield in the above-mentioned synthetic route, and it is a brand-new process route

Method used

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  • Synthesis process of 10-HDA (10-hydroxy-2-decenoic acid)
  • Synthesis process of 10-HDA (10-hydroxy-2-decenoic acid)
  • Synthesis process of 10-HDA (10-hydroxy-2-decenoic acid)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Synthesis of 8-bromo-1-octanol

[0019] Add 7.3 g ( 50 mmol) of 1,8-octanediol, 3.3 ml ( 80 mmol) of hydrobromic acid, 0.15 g of iodine (2% of the main material) and 150 ml of toluene to the reaction flask in sequence, and perform a water separation reaction under stirring After 10 h, toluene was recovered to obtain a yellow mixture. The mixture was separated by column chromatography (ф 8 × L 38 cm), eluted with chloroform:methanol (50:1), and evaporated to dryness in the eluted part of 0.5-1.0 L to obtain a light yellow oil 2， Total 9.62 g, yield 92.5%. Product detection: yellow oil; IRυ cm -1 : 3410 (OH), 2916, 2862 (C-H), 642 (C-Br); 1 H NMR (CDCL 3 ): δ: 3.53 ( t, 2 H, H-8 ), 3.35 (t, 2 H, H-1) , 1.75 (m, 2 H, H-7), 1.45 (m, 2 H, H-2 ), 1.34 (m, 2 H, H-3), 1.24 (m, 6 H, H-(4-6)); ESI-MS m / z 210 [M+H] + (positive mode).

[0020] Synthesis of Bromooctylaldehyde

[0021] Add 6.46 g (30.1 mmol) of 8-bromo-1-octanol and 60 ml of dichloromethane into the r...

Embodiment 2

[0025] Synthesis of 8-bromo-1-octanol

[0026] Add 3.85 g (25 mmol) of 1,8-octanediol, 1.5 ml (35 mmol) of hydrobromic acid, 0.07 g of iodine (2% of the main material) and 75 ml of toluene to the reaction flask in sequence, and perform water separation reaction under stirring After 10 h, toluene was recovered to obtain a yellow mixture. The mixture was separated by column chromatography (ф 8 × L 38 cm), eluted with chloroform:methanol (50:1), and evaporated to dryness in the eluted part of 0.5-1.0 L to obtain a light yellow oil 2， Total 2.40 g, yield 92.3%.

[0027] Synthesis of Bromooctylaldehyde

[0028] Add 2.40 g (11.2 mmol) of 1-bromooctanol and 25 ml of dichloromethane into the reaction flask, add 6.80 g (13 mmol) of PCC into the reaction flask, and react for 2 h while stirring, during which Keep the reaction temperature at 20-30°C. After the reaction is completed, use silica gel column chromatography and vacuum distillation to recover dichloromethane to obtain 1....

Embodiment 3

[0032] Synthesis of 8-bromo-1-octanol

[0033]Add 385 g (2.5 mol) of 1,8-octanediol, 170 ml (4 mol) of hydrobromic acid, 7 g of iodine (2% of the main material) and 7.5 L of toluene in sequence in the reaction flask, and stir for 10 h under water separation Afterwards, toluene was recovered to obtain a yellow mixture. The mixture was separated by column chromatography (ф 15 × L 3.8 m), eluted with chloroform:methanol (50:1), and evaporated to dryness in the eluted part of 0.5-10 L to obtain a light yellow oil 2， Total 240 g, yield 92.3%.

[0034] Synthesis of Bromooctylaldehyde

[0035] Add 240 g (1.12 mol) of 1-bromooctanol and 2.5L methylene chloride into the reaction flask, add 680 g (1.3 mol) of PCC into the reaction flask, and react for 2 h while stirring, during which Keep the reaction temperature at 20-30 °C. After the reaction is completed, use silica gel column chromatography and vacuum distillation to recover dichloromethane to obtain 198 g of yellow oil, with...

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Abstract

The invention relates to a new synthesis process of 10-HDA (10-hydroxy-2-decenoic acid) which comprises the following steps: preparing 8-bromo-1-octanol from 1,8-octanediol and hydrobromic acid under an action of a catalyst with toluene as a solvent; oxidizing 8-bromo-1-octanol with pyridinium chlorochromate in dichloromethane to obtain 8-bromooctanal; reacting obtained 8-bromooctanal with a phosphorus ylides reagent to obtain (2E)-10-bromo-2-decenoic acid; hydrolyzing obtained (2E)-10-bromo-2-decenoic acid in an alkali condition and then acidifying to obtain 10-HDA. The invention provides an industrial synthesis process of 10-HDA, which increases the utilization of atoms, has high purity and yield of 10-HAD and is simple and suitable for industrial production.

Description

technical field [0001] The present invention relates to (2 E )-10-Hydroxy-2-decenoic acid (10-HDA) a new synthesis process. Background technique [0002] Drug name: royal jelly acid, chemical name: (2E)-10-hydroxy-2-decenoic acid, English name: (2E)-10-hydroxydec-2-enoic acid, 10-HDA for short. The chemical structure is: [0003] [0004] Royal jelly acid is a kind of unsaturated fatty acid, which has antibacterial, antibacterial, anti-ulcer, anti-cancer, anti-tumor, anti-radiation and lipid-lowering effects. In recent years. Experts and scholars at home and abroad have conducted various researches and explorations on the methods of synthesizing 10-HDA. There are many synthetic routes, among which there are mainly the following routes: 4 Reduction to get 1,8-octanediol, then Ag 2 CO 3 Selective oxidation of diatomaceous earth to obtain 8-hydroxyoctanal, and finally acetylation with acetic anhydride, condensation with malonic acid, hydrolysis to obtain 10-HDA; ② 8-h...

Claims

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Application Information

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IPC IPC(8): C07C59/42C07C51/367
Inventor 肖艳华
Owner WUHAN INSTITUTE OF TECHNOLOGY
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