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A new method for preparing high-purity hydroxytyrosol

A technology of hydroxytyrosol and dihydroxyphenylacetic acid, which is applied in the field of preparing high-purity hydroxytyrosol, can solve the problems of high vacuum distillation temperature, unsuitable for large batches, long reaction time, etc. Easy to use effect

Active Publication Date: 2021-07-13
TONGHUA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] A synthetic route (WO2008128629) published by DSM that is currently available for industrial production, but this process consumes a large amount of solvent, the reaction time is long, and the vacuum distillation temperature is too high (200°C) is not suitable for large quantities of high-purity hydroxyphenol Production of Alcohol Products

Method used

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  • A new method for preparing high-purity hydroxytyrosol
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  • A new method for preparing high-purity hydroxytyrosol

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Embodiment 1

[0033] A new method for preparing high-purity hydroxybosinol, the synthetic route is as follows:

[0034]

[0035] The new method of preparing high purity hydroxy-oxyxyl alcohol includes the steps of:

[0036] Step 1: Put the hydride lithium in a dry single mouth, add a solvent, and mix well and uniform concentration of 1.5 mol / L solution, spare;

[0037] Step 2: 3,4-dihydroxyacetate is added to the solution at 0 ° C, and 3,4-dihydroxybenzoacetate is added, and the ice bath is removed after the addition is completed, and the reaction is reacted at 100 ° C for 2 h;

[0038] Step 3: After the reaction is completed at 0 ° C, slowly drop the water and concentrated a hydrochloric acid solution, and then extracted 2 times with ethyl acetate, combined with an organic phase, then washed with aqueous sodium bicarbonate 4 times, then dried over anhydrous magnesium sulfate, filtrate, evaporated, evaporated, the solvent was evaporated, and the light yellow oil is hydroxybylol. The prepara...

Embodiment 2

[0044] A new method for preparing high-purity hydroxybosinol, the synthetic route is as follows:

[0045]

[0046] The new method of preparing high purity hydroxy-oxyxyl alcohol includes the steps of:

[0047] Step 1: Put the hydride lithium in a dry single mouth bottle, add a solvent, and thoroughly mix the concentration of 1.8 mol / L, spare;

[0048] Step 2: 3,4-dihydroxybenzoic acid is added to the solution at 0 ° C, and 3,4-dihydroxytobenylacetic acid was added, and the ice bath was removed after the addition was added, and the reaction was reacted at 60 ° C for 12 h;

[0049] Step 3: After the reaction, the reaction solution was placed at 0 ° C, slowly dropped the water and concentrated a hydrochloric acid solution, and then extracted 3 times with ethyl acetate, combined with aqueous sodium hydrogencarbonate, then washed with aqueous sodium bicarbonate Three times, then dried over anhydrous magnesium sulfate, filtrate, evaporated to the solvent under reduced pressure, and ...

Embodiment 3

[0052] A new method for preparing high-purity hydroxybosinol, the synthetic route is as follows:

[0053]

[0054] The new method of preparing high purity hydroxy-oxyxyl alcohol includes the steps of:

[0055] Step 1: Put the hydride lithium in a dry single mouth bottle, add a solvent, and thoroughly mix the concentration of 1.8 mol / L, spare;

[0056] Step 2: 3,4-dihydroxybenzoic acid is added to the solution at 0 ° C, and 3,4-dihydroxytobenylacetic acid was added, and the ice bath was removed after the addition was added, and the reaction was reacted at 60 ° C for 12 h;

[0057] Step 3: After the reaction, the reaction solution was placed at 0 ° C, slowly dropped the water and concentrated a hydrochloric acid solution, and then extracted 3 times with ethyl acetate, combined with aqueous sodium hydrogencarbonate, then washed with aqueous sodium bicarbonate Three times, then dried over anhydrous magnesium sulfate, filtrate, evaporated, evaporated to evaporase, to give a light y...

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Abstract

The invention discloses a new method for preparing high-purity hydroxytyrosol, which belongs to the technical field of pharmaceutical chemical synthesis. The specific steps of the method are: uniformly mixing lithium aluminum hydride with a solvent, and then adding 3,4-dihydroxyphenylacetic acid in batches Carry out the reaction, place the reaction solution at 0°C after the reaction is completed, slowly add water and hydrochloric acid solution dropwise, extract with ethyl acetate after dropping, combine the organic phases, wash with aqueous sodium bicarbonate solution, and dry over anhydrous magnesium sulfate After that, the salt was removed by suction filtration, and the solvent was evaporated under reduced pressure to obtain a light yellow oily substance which was hydroxytyrosol. The beneficial effects are: the raw materials of the new preparation method of the present invention are easy to obtain, the cost is low, the operation is simple, and 3,4-dihydroxyphenylacetic acid can be reduced to hydroxytyrosol in one step, the reaction rate is fast, the yield of the target product is high, and no column chromatography is required Purification can produce high-purity hydroxytyrosol, which is suitable for industrial production.

Description

Technical field [0001] The present invention relates to the field of pharmaceutical synthesis, and in particular, a new method involving preparation of high purity hydroxypartriesol. Background technique [0002] Hydroxy-fine alcohol, also known as 3,4-dihydroxy phenylethyl alcohol, is a polyphenolic compound having strong antioxidation in olives, and is also a metabolite of animal brain dopamine. Studies have shown that hydroxybylol has good biological activity, mainly including broad-spectrum antimicrobial activity, prevents direct damage to multiple free radicals, prevents diabetes and improves adipose tissue to insulin sensitivity, and reduce atherosclerosis Range and prevent myocardial ischemia / reperfusion injury, improve β-amyloid-induced Alzheimerism, and inhibit tumor proliferation. Many foreign institutions have added hydroxybosiniol as additives to health products and food, and found that there is a good effect of anti-aging and preventing diseases. [0003] At presen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/147C07C39/11
CPCC07C29/147C07C39/11
Inventor 臧皓徐倩张露云徐晶夏广清朱俊义
Owner TONGHUA NORMAL UNIV
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