Salicylaldehyde derivatives and preparation method thereof

A derivative, salicylaldehyde technology, applied in the field of salicylaldehyde derivatives and their preparation, can solve the problems of low efficiency, unfriendly environment, high cost, and achieve the effects of complex and diverse structures and broad application prospects.

Active Publication Date: 2014-08-20
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] Using salicyl alcohol as raw material to produce salicylaldehyde mainly includes salicyl alcohol liquid-phase catalytic oxidation method and electro-oxidation method. However, the liquid-phase catalytic oxidation method requires the use of noble metal catalysts, and the electro-oxidation method is not efficient.
[0021] In summary, the method for preparing salicylaldehyde in the prior art has disadvantages such as high cost, low efficiency and unfriendly environment
Looking at the history of scientific research, there are many kinds of salicylaldehyde derivatives, and their preparation is still in the exploratory stage, and there is no systematic preparation system.

Method used

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  • Salicylaldehyde derivatives and preparation method thereof
  • Salicylaldehyde derivatives and preparation method thereof
  • Salicylaldehyde derivatives and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] A salicylaldehyde derivative, the structural formula of the salicylaldehyde derivative is:

[0057]

[0058] A kind of preparation method of salicylaldehyde derivative, described preparation method comprises the following steps:

[0059] a. Precursor compound synthesis;

[0060] b. Synthesis of the target product;

[0061] c. Purification.

[0062] Wherein, a, precursor compound is synthesized, comprises the following steps:

[0063] (1) Using sodium hydride as a catalyst, add 200mmol dimethyl malonate and 440mmol propargyl bromide into anhydrous acetonitrile in an ice-water bath, stir and react for 8 hours, wash the product with water, extract with ethyl acetate, spin under reduced pressure Dry, column chromatography (volume ratio ethyl acetate: petroleum ether = 1:100) to obtain a white solid product;

[0064] (2) Mix 80mmol of compound 1 with 240mmol of phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, the molar ratio...

Embodiment 2

[0076] A salicylaldehyde derivative, the structural formula of the salicylaldehyde derivative is:

[0077]

[0078] A kind of preparation method of salicylaldehyde derivative, described preparation method comprises the following steps:

[0079] a. Precursor compound synthesis;

[0080] b. Synthesis of the target product;

[0081] c. Purification.

[0082] Wherein, a, precursor compound is synthesized, comprises the following steps:

[0083] (1) Using sodium hydride as a catalyst, add 200mmol dibenzyl malonate and 600mmol propargyl bromide into anhydrous acetonitrile in an ice-water bath, stir and react for 8 hours, wash the product with water, extract with ethyl acetate, and depressurize Spin dry, column chromatography (volume ratio ethyl acetate:petroleum ether=1:80) to obtain a white solid product;

[0084] (2) Mix 80mmol of compound 1 with 180mmol of phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, the molar ratio Pd(PPh ...

Embodiment 3

[0096] A salicylaldehyde derivative, the structural formula of the salicylaldehyde derivative is:

[0097]

[0098] A kind of preparation method of salicylaldehyde derivative, described preparation method comprises the following steps:

[0099] a. Precursor compound synthesis;

[0100] b. Synthesis of the target product;

[0101] c. Purification.

[0102] Wherein, a, precursor synthesis, comprises the following steps:

[0103] (1) Using sodium hydride as a catalyst, add 200mmol diisopropyl malonate and 460mmol propargyl bromide into anhydrous acetonitrile in an ice-water bath, stir and react for 8 hours, wash the product with water, extract with ethyl acetate, and remove Press and spin dry, column chromatography (volume ratio ethyl acetate: petroleum ether = 1:80) to obtain a white solid product;

[0104] (2) Mix 80mmol of compound 1 with 200mmol of 4-fluorophenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, the molar ratio Pd(...

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Abstract

The present invention provides salicylaldehyde derivatives and a preparation method thereof. The preparation method comprises: a, precursor synthesis; b, target product synthesis; and c, purification. Compared with the salicylaldehyde derivative and the preparation method thereof in the prior art, the salicylaldehyde derivative and the preparation method thereof of the present invention have the following characteristics that: the completely-new poly-substituted salicylaldehyde derivative synthesis method is provided, a series of the new salicylaldehyde derivatives are produced, and compared with the ordinary salicylaldehyde derivative, the prepared salicylaldehyde derivative of the present invention has multiple rings so as to have the complex and diverse structure, and presents wide application prospects in chemical engineering production and clinical medicine.

Description

technical field [0001] The invention relates to the field of organic compounds, in particular to salicylaldehyde derivatives and a preparation method thereof. Background technique [0002] Salicylaldehyde and its derivatives are widely used in industrial production and scientific research. For example, salicylaldehyde and its derivatives are important intermediates in organic synthesis and fine chemicals, and are widely used in pesticides, medicines, spices, chelating agents, and dye intermediates and other fields. In view of the special importance of salicylaldehyde and its derivatives, how to expand the synthetic route of salicylaldehyde and its derivatives has aroused the active thinking of countless organic synthesizers and chemists, and came up with some very effective methods. [0003] Common salicylaldehyde synthesis methods are mainly divided into four categories from the perspective of raw materials: using phenol, o-cresol, salicylic acid and salicyl alcohol as raw...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/757C07C67/313
CPCC07C67/313C07C69/757C07C2602/08
Inventor 胡益民胡亚东
Owner ANHUI NORMAL UNIV
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