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The synthetic preparation method of 2,6-dinitrobenzaldehyde

A technology of dinitrobenzene and dinitrotoluene, applied in the field of synthesis and preparation of 2,6-dinitrobenzaldehyde, can solve the problems of harsh reaction conditions, difficult industrial production, serious pollution, etc., and achieve easy operation , short cycle and simple process

Inactive Publication Date: 2011-12-28
HENAN DONGTAI PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are many ways to prepare 2,6-dinitrobenzaldehyde, basically 2,6-dinitrotoluene is used as raw material, but due to the relatively large steric hindrance of the two nitro groups, it is difficult to directly oxidize Methyl becomes aldehyde
[0003] Chemische Berichte. 1912, 45, 804; 1925, 58, 1373 Provide a kind of synthetic method of 2,6-dinitrobenzyl bromide, Journal of the Chemical Society; (1957); p. 3807 Provides a method for generating 2,6-dinitrobenzaldehyde from 2,6-dinitrobenzyl bromide, but 2,6-dinitrobenzyl bromide is produced by directly reacting 2,6-dinitrobenzyl bromide with liquid bromine , the reaction conditions in this step are harsh, the pollution caused is serious, and the yield is low, so it is difficult to apply to large-scale industrial production

Method used

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  • The synthetic preparation method of 2,6-dinitrobenzaldehyde

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Embodiment 1

[0021] The preparation of embodiment 1 2,6-dinitrobenzaldehyde

[0022] Dissolve 2,6-dinitrotoluene (9.10g, 0.05mol) and DFA (35.70g, 0.3mol) in 90ml of organic solvent dioxane, heat at 100°C for 8 hours, and concentrate and evaporate to dryness after the reaction Then add dichloromethane, add 0.5g of activated carbon, pass oxygen at normal pressure and room temperature, filter after the oxidation reaction is completed, concentrate the filtrate to dryness, and recrystallize in ethanol to obtain 6.4g of 2,6-dinitrobenzaldehyde yellow solid , yield 65.3%. The resulting product Mp (melting point) 120-122°C.

Embodiment 2

[0023] Example 2 Preparation of 2,6-dinitrobenzaldehyde

[0024] 2,6-Dinitrotoluene (9.10 g, 0.05 mol) and DFA (35.70 g, 0.3 mol) were dissolved in 50 ml of organic solvent DMF, and heated at 100°C for 8 hours. After the reaction is completed, concentrate and evaporate to dryness, then add it to dichloromethane, add 0.5g of activated carbon, and pass through oxygen at normal pressure and room temperature, filter after the oxidation reaction is completed, concentrate the filtrate to dryness, and recrystallize in ethanol to obtain 2,6-dinitrate 6.2 g of benzaldehyde yellow solid, yield 63.2%. Mp 121-123°C.

Embodiment 3

[0025] Example 3 Preparation of 2,6-dinitrobenzaldehyde

[0026] 2,6-Dinitrotoluene (9.10 g, 0.05 mol) and DFA (35.70 g, 0.3 mol) were dissolved in 50 ml of organic solvent DMF, and heated at 100°C for 8 hours. After the reaction is completed, concentrate and evaporate to dryness, then add to methanol, add 0.5g of activated carbon, pass through oxygen at normal pressure and room temperature, filter after the oxidation reaction is completed, concentrate the filtrate to dryness, and recrystallize in ethanol to obtain 2,6-dinitrobenzene Formaldehyde yellow solid 6.5g, yield 66.3%. Mp 122-123°C.

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Abstract

The invention relates to a preparation method of 2,6-dinitrobenzaldehyde. In the method, 2,6-dinitrotoluene DFA reacts to generate olefins, and then directly oxidizes 2,6-dinitrobenzaldehyde with oxygen under the action of a catalyst. The synthesis method of the invention has mild reaction conditions, simple and convenient operation, low cost, high product yield and good purity, overcomes the shortcomings of the prior art, and is suitable for industrialized batch production.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis and relates to a synthesis and preparation method of 2,6-dinitrobenzaldehyde. Background technique [0002] 2,6-Dinitrobenzaldehyde is an important pharmaceutical intermediate, for example, it is an important raw material for the synthesis of 9-nitrocamptothecin and 9-aminocamptothecin. There are many ways to prepare 2,6-dinitrobenzaldehyde, basically 2,6-dinitrotoluene is used as raw material, but due to the relatively large steric hindrance of the two nitro groups, it is difficult to directly oxidize The methyl group becomes an aldehyde group. [0003] Chemische Berichte. 1912, 45, 804; 1925, 58, 1373 Provide a kind of synthetic method of 2,6-dinitrobenzyl bromide, Journal of the Chemical Society; (1957); p. 3807 Provides a method for generating 2,6-dinitrobenzaldehyde from 2,6-dinitrobenzyl bromide, but 2,6-dinitrobenzyl bromide is produced by directly reacting 2,6-dinitrobenzyl ...

Claims

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Application Information

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IPC IPC(8): C07C205/44C07C201/12
Inventor 苗青杨向阳李志江
Owner HENAN DONGTAI PHARM
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