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Preparation method of anti-nash drug intermediate dialdehyde group magnolol

A magnolol and dialdehyde-based technology, applied in the field of organic synthesis, can solve problems such as difficult separation and purification, low yield, and many by-products, and achieve the effects of being beneficial to industrial production, reducing production costs, and reducing reaction by-products

Active Publication Date: 2021-11-30
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are many shortcomings in this method, such as poor selectivity of the reaction, both monoaldehyde magnolol and bisaldehyde magnolol in the product, many by-products, difficult separation and purification, and low yield. In addition, using The Reimer-Tiemann reaction method not only has the problem of low yield, but also requires the use of a large amount of volatile organic solvent chloroform, which leads to higher production costs and greater pressure on environmental protection

Method used

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  • Preparation method of anti-nash drug intermediate dialdehyde group magnolol
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  • Preparation method of anti-nash drug intermediate dialdehyde group magnolol

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Experimental program
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Effect test

Embodiment 1

[0030] The preparation method of the anti-NASH drug intermediate dialdehyde group magnolol of the present embodiment, described method comprises the steps:

[0031] In a 50 ml round bottom flask, magnolol (1.064 g, 4.0 mmol) was added at room temperature. Weigh hexamethylenetetramine (1.1216g, 8.0mmol) and dissolve it in glacial acetic acid (2mL), add it together to the flask, slowly heat up to 130°C and stir for 3 hours, then cool down to 100°C, add sulfuric acid solution ( 33%, w / w, 0.2mL), continued to stir for 1 hour, cooled to room temperature, added diethyl ether to extract 3 times, washed with brine, dried over anhydrous sodium sulfate, and removed the solvent under reduced pressure to obtain a residue, which was separated by column chromatography (ethyl acetate ester / petroleum ether, 1:60) to obtain the target product 5,5'-diallyl-2,2'-dihydroxy-[1,1'-biphenyl]-3,3'-dicarbaldehyde, the yield 73.3%.

[0032] The HPLC detection result of the above-mentioned synthetic p...

Embodiment 2

[0036] The preparation method of the anti-NASH drug intermediate dialdehyde group magnolol of the present embodiment, described method comprises the steps:

[0037]In a 50 ml round bottom flask, magnolol (0.2660 g, 1.0 mmol) was added at room temperature. Weigh hexamethylenetetramine (0.0701g, 0.5mmol) and dissolve it in glacial acetic acid (2mL), add it together to the flask, slowly heat up to 130°C and stir for 3 hours, then cool down to 100°C, add sulfuric acid solution ( 33%, w / w, 2mL), continued to stir for 1 hour, cooled to room temperature, added diethyl ether to extract 3 times, washed with brine, dried over anhydrous sodium sulfate, and removed the solvent under reduced pressure to obtain a residue, which was separated by column chromatography (ethyl acetate / petroleum ether, 1:60) to obtain the target product 5,5'-diallyl-2,2'-dihydroxy-[1,1'-biphenyl]-3,3'-dicarbaldehyde in a yield of 76.2 %, the purity is 99.1% (HPLC detection wavelength: 254nm, mobile phase is 40...

Embodiment 3

[0039] The preparation method of the anti-NASH drug intermediate dialdehyde group magnolol of the present embodiment, described method comprises the steps:

[0040] In a 50 ml round bottom flask, magnolol (0.2660 g, 1.0 mmol) was added at room temperature. Weigh hexamethylenetetramine (0.2804g, 2.0mmol) and dissolve it in glacial acetic acid (2mL), add it to the flask together, slowly raise the temperature to 130°C and stir for 1 hour, then cool down to 100°C, add sulfuric acid solution ( 33%, w / w, 2mL), continued to stir for 1 hour, cooled to room temperature, added diethyl ether to extract 3 times, washed with brine, dried over anhydrous sodium sulfate, and removed the solvent under reduced pressure to obtain a residue, which was separated by column chromatography (ethyl acetate / petroleum ether, 1:60) to obtain the target product 5,5'-diallyl-2,2'-dihydroxy-[1,1'-biphenyl]-3,3'-dicarbaldehyde, the yield was 60.6 %, the purity is 98.9% (HPLC detection wavelength: 254nm, mob...

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Abstract

The invention relates to a preparation method of bisaldehyde magnolol, an anti-NASH drug intermediate, and belongs to the technical field of organic synthesis. The preparation method of the present invention specifically comprises: under room temperature conditions, adding magnolol into the round bottom flask; weighing an appropriate amount of hexamethylenetetramine, adding it to glacial acetic acid, stirring and mixing evenly, adding the mixed solution into the flask, slowly Raise the temperature to 130°C, stir and react at constant temperature for 1-3 hours, after the reaction, cool to 100°C; add dilute sulfuric acid solution to the flask, continue to stir and react for 0.5-3 hours, cool to room temperature, then extract, wash with brine, dry, The solvent was removed under reduced pressure to obtain a residue, which was finally separated by column chromatography to obtain the target product. The yield and purity of the target product of the present invention are high, and the present invention uses cheap and easy-to-obtain glacial acetic acid as the organic solvent, does not use toxic organic solvents such as chloroform or trifluorobenzene, the environmental protection pressure is small, the production cost is reduced, and it is beneficial to industrialization Production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of bisaldehyde magnolol, an anti-NASH drug intermediate, more specifically, the invention relates to 5,5'-diallyl-2,2'-diallyl Preparation method of hydroxy-[1,1'-biphenyl]-3,3'-dicarbaldehyde. Background technique [0002] Magnolia officinalis is the dried dry bark, root bark and branch bark of Magnolia officinalis Rehd. et Wils. or Magnolia officinalis Rehd. et Wils. var. biloba Rehd. et Wils. Clinically, it is mainly used to treat apoplexy, typhoid fever, headache, chills and palpitations, qi and blood numbness, warming the middle and replenishing qi, eliminating phlegm and lowering qi, treating cholera, abdominal pain and fullness, cold and upset stomach, and removing hot heart and depression. According to reports, Magnolia officinalis contains at least more than two hundred different components, and magnolol and honokiol are its main pharmacolog...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/42C07C47/57
CPCC07C45/42C07C47/57
Inventor 任家强陈祺穆岩段梦瑶韩凤梅陈勇
Owner HUBEI UNIV