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Synthesis method for hydroxytyrosol

A synthesis method and technology for hydroxytyrosol, applied in chemical instruments and methods, preparation of organic compounds, organic compounds/hydrides/coordination complex catalysts, etc. It can solve the problems of solvent residue, good selectivity and easy post-treatment, etc.

Active Publication Date: 2021-03-09
SHENZHEN DIECKMANN TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In a word, the current synthetic route is long, the yield is low, and the cost is high, and the reagents used are thionyl chloride, bromine, and boron tribromide, which are neither environmentally friendly nor safe, and the environment is destructive. The requirements for equipment are also high. High, aluminum lithium hydrogen is an expensive and unsafe reagent in industry
Because hydroxytyrosol is a viscous oily liquid, the solvent residue is extremely difficult to remove, and the ordinary distillation method is inconsistent with the stability of hydroxytyrosol, and the cost is too high if it is completely dependent on column chromatography
Therefore, none of the existing methods provides a good purification scheme for hydroxytyrosol

Method used

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  • Synthesis method for hydroxytyrosol
  • Synthesis method for hydroxytyrosol
  • Synthesis method for hydroxytyrosol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] 1, the preparation of 3-bromo-4-hydroxyphenethyl alcohol

[0054]

[0055] Add 69.1g (0.5mol) of 4-hydroxyphenethyl alcohol, 500mL of water, and 200mL of acetone into the three-neck flask respectively. Install an ice-water bath, lower the temperature to below 15°C, and add 250 g (0.407 mol) of potassium monopersulfate compound salt in batches. Slowly add a pre-prepared 50 wt% sodium bromide aqueous solution (containing 51.5 g of sodium bromide, 0.5 mol) dropwise, and control the temperature below 20°C. After the dropwise addition was completed, the reaction was continued for 1 hour in an ice-water bath. TLC analysis (developing agent PE: EA = 2: 1), after the reaction is completed, slowly add 39.5 g (0.25 mol) of sodium thiosulfate in batches under an ice-water bath to quench the reaction, after the addition is complete, pour the reaction solution into In the single-necked bottle, acetone was evaporated under reduced pressure below 45°C, crystals were precipitated,...

Embodiment 2

[0064] 1, the preparation of 3-bromo-4-hydroxyphenethyl alcohol

[0065] Add 1mol 4-hydroxyphenylethanol, 1000mL water, and 400mL acetone into the three-neck flask respectively. Install an ice-water bath, lower the temperature to below 5°C, and add 2 mol of potassium monopersulfate compound salt in batches. Slowly add a pre-prepared 50 wt% potassium bromide aqueous solution (containing 2 mol of potassium bromide) dropwise, and control the temperature below 5°C. After the dropwise addition was completed, the reaction was continued for 2 hours in an ice-water bath. TLC analysis (developing agent PE: EA = 2: 1), after the reaction is completed, slowly add 0.8 mol of sodium thiosulfate in batches to quench the reaction under an ice-water bath, after the addition is completed, pour the reaction solution into a one-mouth bottle, The acetone was distilled off under reduced pressure below 45°C, and crystals were precipitated, filtered with suction, washed with water, and dried in a ...

Embodiment 3

[0069] 1, the preparation of 3-bromo-4-hydroxyphenethyl alcohol

[0070] Add 1mol 4-hydroxyphenylethanol, 1000mL water, and 500mL acetone into the three-neck flask respectively. Install an ice-water bath, lower the temperature to below 10°C, and add 1 mol of potassium monopersulfate compound salt in batches. Slowly add a pre-prepared 50 wt% sodium bromide aqueous solution (containing 3 mol of sodium bromide) dropwise, and control the temperature below 10°C. After the dropwise addition was completed, the reaction was continued for 3 hours in an ice-water bath. TLC analysis (developing agent PE: EA = 2: 1), after the reaction is completed, slowly add 1 mol of sodium bisulfite in batches to quench the reaction under an ice-water bath. Acetone was distilled off under reduced pressure below 45°C, and crystals were precipitated. Suction filtration, washing with water, and drying in a blast drying oven gave 0.8891 mol of the product, with a molar yield of 88.91%.

[0071] 2, Prepa...

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Abstract

The invention belongs to the field of organic synthesis, and discloses a synthesis method for hydroxytyrosol. The method comprises a step b that: a reaction is carried out on 3-bromine-4-hydroxy phenylethanol, an alkali metal hydroxide and a copper catalyst, wherein the copper catalyst is at least one selected from 8-hydroxyquinoline copper, copper acetylacetonate and BFMO-cuprous iodide. According to the process route, hydroxyl protection and deprotection steps are omitted, bromine does not need to be replaced with methoxyl, hydroxyl substitution is achieved in a sodium hydroxide aqueous solution under catalysis of the copper catalyst, and therefore, selectivity is good, the reaction route is short, the product can be obtained only through two steps, and the problem that an existing process route is too long is solved.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing hydroxytyrosol. Background technique [0002] Hydroxytyrosol, also known as hydrated tyrosine, 2-(3,4-dihydroxyphenyl)-ethanol, 3,4-dihydroxyphenylethanol, 4-(2-hydroxyethyl)-1,2-benzene diphenols. Hydroxytyrosol was first extracted and isolated from olive oil known as "liquid platinum" and "Mediterranean nectar". In nature, it is mainly distributed in olive fruits and olive leaves, but many plants found so far also contain Hydroxytyrosol ingredients, such as lilac leaves, Korean clove leaves, etc., all contain active ingredients of hydroxytyrosol. There are two hydroxyl groups connected to the benzene ring of hydroxytyrosol, which is the main antioxidant active group. Its various biological functions are mostly related to its antioxidant activity as a polyphenol. Studies have shown that in addition to its strong antioxidant effect, hydroxytyrosol is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/02C07C39/11B01J31/22
CPCB01J31/2217B01J31/2226B01J31/2234B01J2231/4288B01J2531/16C07C37/02C07C37/62C07C39/11C07C39/245
Inventor 杨超文王蕾宋家良关志帅符定良
Owner SHENZHEN DIECKMANN TECH CO LTD
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