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A kind of synthetic method of substituted pyrogallol

A synthesis method and pyrogallol technology are applied in the field of synthesis of substituted pyrogallol compounds, can solve the problems of short reaction steps, harsh raw material sources and the like, and achieve the effects of mild reaction conditions, easy products and high yields

Active Publication Date: 2017-08-01
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is environmentally friendly, the raw materials are easy to obtain, the reaction steps are short, and it is convenient for industrialization. The disadvantage is that the source of raw materials is still harsh for the preparation of some complex polyphenols containing substituents.

Method used

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  • A kind of synthetic method of substituted pyrogallol
  • A kind of synthetic method of substituted pyrogallol
  • A kind of synthetic method of substituted pyrogallol

Examples

Experimental program
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Effect test

example 1

[0013] Example 1: Synthesis of 5-methylpyrogallol

[0014]

[0015] The mass ratio of the feed material 2-(4-methylphenoxy)pyridine: palladium acetate: iodobenzene diacetate is: 1:0.05:3, the organic solvent is acetonitrile, and the solvent consumption is 0.1mol / L (2-(4- methylphenoxy)pyridine molar concentration).

[0016] In a three-necked flask equipped with a thermometer, a reflux condenser and mechanical stirring, 1.85 g (0.01 mol) of 2-(4-methylphenoxy) pyridine, 0.11 g (0.5 mmol) of palladium acetate, and diacetic acid were added successively at room temperature. Iodobenzene 9.66g (0.03mol) and acetonitrile 100mL. After the addition, the temperature was raised to 60° C., and the reaction was maintained for 12 hours. After the reaction, the solvent was evaporated under reduced pressure, the residue was poured into ice water, extracted with ethyl acetate, washed with deionized water, and distilled under reduced pressure to obtain a crude product, which was recrystall...

example 2

[0019] Example 2: Synthesis of 5-chloropyrogallol

[0020]

[0021] The mass ratio of the feed material is 2-(4-chlorophenoxy)pyridine: palladium chloride: iodobenzene diacetate: 1:0.05:3, the organic solvent is N,N-dimethylacetamide, and the solvent consumption is 1mol / L (2-(4-chlorophenoxy)pyridine molar concentration).

[0022] In a three-necked flask equipped with a thermometer, a reflux condenser and mechanical stirring, 1.85 g (0.01 mol) of 2-(4-methylphenoxy) pyridine, 0.09 g (0.5 mmol) of palladium chloride, and di 9.66g (0.03mol) of iodobenzene acetate and 10mL of N,N-dimethylacetamide. After the addition was completed, the temperature was raised to 120° C., and the reaction was maintained for 3 hours. After the reaction, the solvent was evaporated under reduced pressure, the residue was poured into ice water, extracted with ethyl acetate, washed with deionized water, and distilled under reduced pressure to obtain a crude product, which was recrystallized from t...

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Abstract

The invention relates to a synthesis method of substituted pyrogallols, belonging to the field of organic synthesis. The method comprises the following steps: by using aryloxy pyridines as a raw material, carrying out reaction in an organic solvent at 60-120 DEG C under the actions of a palladium catalyst and iodosobenzene diacetate for 3-12 hours to obtain a diacetyl oxidation product; and finally, carrying out treatment to remove acetyl and pyridyl to obtain the pyrogallol compounds. The method has the advantages of mild reaction conditions, high yield and no exhaust pollution, is easy to operate, can easily implement scale-up production, and has favorable application prospects.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a synthesis method of a substituted pyrogallol compound. Background technique [0002] Polyphenols are an important class of organic intermediates, which have good antitumor activity and antibacterial activity, and are widely used in the field of medicine. Before the present invention is provided, there are certain reports on the synthesis method of existing polyhydric phenols. Taking pyrogallol as an example, the aromatic aldehydes substituted with hydroxyl groups are usually used as reaction raw materials. After Dakin reaction, in hydrogen peroxide and strong alkali system Preparation (Formula 1, route a, B. Saikia, P. Borah and N. C. Barua, Green Chem. 2015, 17, 4533-4536). However, the sources of raw materials involved in this type of reaction are relatively difficult, and the reagents used are relatively corrosive and polluted, and there are great safety hazards in the use pro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B41/02C07C37/055C07C39/10C07C39/28
CPCC07B41/02C07C37/055C07C37/0555C07D213/643C07C39/10C07C39/28
Inventor 王亮潘亮陈群何明阳
Owner CHANGZHOU UNIV
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