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Method for synthesizing o-nitrobenzaldehyde compounds

A technology of o-nitrobenzaldehyde and its synthesis method, which is applied in the field of synthesis of o-nitrobenzaldehyde compounds, can solve problems such as difficult large-scale industrial production, and achieve the effect of simple operation and mild reaction conditions

Active Publication Date: 2008-07-16
SHANGHAI CHEMPARTNER CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, this method is difficult to apply to large-scale industrial production

Method used

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  • Method for synthesizing o-nitrobenzaldehyde compounds
  • Method for synthesizing o-nitrobenzaldehyde compounds
  • Method for synthesizing o-nitrobenzaldehyde compounds

Examples

Experimental program
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Embodiment 1

[0017] Embodiment 1 prepares 2-nitro-3-chlorobenzaldehyde

[0018] At room temperature, 2-nitro-3-chlorobenzyl alcohol (9.4g, 0.05mol), dichloromethane (100mL), BAIB (17.7g, 0.055mol) and TEMPO (0.75g, 5mmol) were successively added to the reaction flask , Stir evenly and then stir at 25-30°C until TLC traces the reaction of raw materials to complete (8h). After the reaction, add water (100mL) to the reaction solution, stir well and extract with dichloromethane (3×100mL), combine the organic phases, dry with anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain 2-nitro-3- Chlorobenzaldehyde, the yield is 86%.

Embodiment 2

[0019] Embodiment 2 prepares 2-nitro-6-chlorobenzaldehyde

[0020] At room temperature, add 2-nitro-6-chlorobenzyl alcohol (9.4g, 0.05mol), chloroform (120mL), BAIB (40.1g, 0.125mol) and TEMPO (0.40g , 2.5mmol), stirred evenly and reacted at 10-15°C to TLC to track the complete reaction of raw materials (12h). After the reaction, add water (100mL) to the reaction solution, stir well and extract the aqueous phase with dichloromethane (3×100mL), concentrate and evaporate the organic solvent to obtain 2-nitro-6-chlorobenzaldehyde with a yield of 86%. .

Embodiment 3

[0021] Embodiment 3 prepares 2-nitro-6-bromobenzaldehyde

[0022] At room temperature, add 2-nitro-6-bromobenzyl alcohol (11.6g, 0.05mol), 1,1,2-trichloroethane (100mL), BAIB (24.1g, 0.075 mol) and TEMPO (1.5g, 10mmol), stirred evenly and then stirred at 35-40°C until TLC followed the complete reaction of the raw materials (7h). After the reaction, add water (100mL) to the reaction solution, stir well and extract the aqueous phase with dichloromethane (3×100mL), concentrate and evaporate the organic solvent to obtain 2-nitro-6-bromobenzaldehyde with a yield of 88%. .

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Abstract

The invention discloses a synthesis method for an o-Nitrobenzaldehyde compound which is showed in formula I. The method has the following steps: leading a halogenated 2-nitrobenzenemethanol showed in formula II to carry out oxidation reaction with a mixed oxidant of a 2, 2, 6, 6-tetramethylpiperidinooxy and an iodosobenzen ediacetate. The method of the invention is simple in operation, and the reaction condition is gentle, which is not only suitable for small-scale production in laboratory, but also suitable for large-scale industry production, wherein, X relates to Cl, Br, I or F, which is in a third, fourth, fifth or sixth place.

Description

technical field [0001] The invention relates to a synthesis method of o-nitrobenzaldehyde compounds. Background technique [0002] O-nitrobenzaldehyde compounds are a very important class of chemical intermediates, especially in the industries of medicine, pesticides, dyes, spices, cosmetics and so on. A.T.Hewson (J.Chem.Soc.Perkin Trans.1, 1991, p1565) and others reported that 2-bromo-6-nitrotoluene was used as a raw material to prepare 2-bromo-6-nitrotoluene through multi-step reactions such as methyl bromination. 6-Nitrobenzaldehyde. In this method, it is necessary to use flammable, explosive and highly carcinogenic nitroso compounds as raw materials, which is harmful to the environment and the health of workers; and the post-treatment of the reaction waste liquid is troublesome, and the labor protection conditions are harsh. Therefore, this method is difficult to apply to large-scale industrial production. Contents of the invention [0003] The object of the present...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/44
Inventor 刘国斌李原强章云海唐曦
Owner SHANGHAI CHEMPARTNER CO LTD
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