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O-nitrophenylacetic acid and catalysis synthesis of phase transfer

A technology of phase transfer catalysis and nitrophenylacetic acid, which is applied in the field of synthesis of o-nitrophenylacetic acid to achieve the effects of less by-products, mild reaction conditions, and reduced side reactions

Inactive Publication Date: 2003-12-24
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is still in the stage of laboratory research

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach 1

[0019] Take 1 g of a gel polystyrene-supported tributylbenzyl chloride catalyst with a cross-linking degree of 4%, swell with toluene for 1 h, and add o-nitrobenzyl chloride and NaCN at a ratio of 1:1.1 at 80 °C. , the stirring speed is 600rmp, the reaction is 4h, o-nitrophenylacetonitrile is generated first, then 30% NaOH solution is added to the system, and the hydrolysis is carried out under alkaline conditions. After 2h, the reaction solution is taken out, the resin is filtered out, washed with water , dry, and store for reuse. The filtrate is allowed to stand for stratification, and then the water phase is taken out, washed with acid, filtered, and the filter cake is naturally dried to obtain the product o-nitrophenylacetic acid. The yield was 88%.

Embodiment approach 2

[0021] Take 1 g of gel polystyrene-supported tripropylbenzyl chloride catalyst with a cross-linking degree of 4%, swell with toluene for 1 h, and add o-nitrobenzyl chloride and NaCN in a ratio of 1:1.1 at 80 °C, The stirring speed is 600rmp, and the reaction is carried out for 4h. First, o-nitrophenylacetonitrile is generated. Then, 30% NaOH solution is added to the system, and the hydrolysis is carried out under alkaline conditions. After 2h, the reaction solution is taken out, and the resin is filtered out, washed with water, Dry and store for reuse. The filtrate is allowed to stand for stratification, and then the water phase is taken out, washed with acid, filtered, and the filter cake is naturally dried to obtain the product o-nitrophenylacetic acid. The yield was 64%.

Embodiment approach 3

[0023] Take 1 g of a gel polystyrene-supported trimethylbenzyl chloride catalyst with a cross-linking degree of 4%, swell with toluene for 1 hour, and add o-nitrobenzyl chloride and NaCN at a ratio of 1:1.1 at 80 °C. , the stirring speed is 600rmp, the reaction is 4h, o-nitrophenylacetonitrile is generated first, then 30% NaOH solution is added to the system, and the hydrolysis is carried out under alkaline conditions. After 2h, the reaction solution is taken out, the resin is filtered out, washed with water , dry, and store for reuse. The filtrate is allowed to stand for stratification, and then the water phase is taken out, washed with acid, filtered, and the filter cake is naturally dried to obtain the product o-nitrophenylacetic acid. The yield was 31%.

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PUM

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Abstract

An o-nitrophenylacetic acid is prepared through reaction of o-nitro benzyl chloride on sodium cyanide under the action of high polymer carried phase transfer catalyst (quaternary ammonium salt) to generate o-nitro phenylacetonitrile, adding solution of NaOH, and hydrolyzing. Its advantages are gentle reaction condition and high output rate.

Description

technical field [0001] The invention of o-nitrophenylacetic acid and phase transfer catalytic synthesis is a method for synthesizing o-nitrophenylacetic acid in a phase transfer catalytic system, and belongs to the technical field of organic synthesis and environment-friendly chemical process. technical background [0002] Nitrophenylacetic acid is an excellent herbicide, around which a series of drugs and fine chemical products can be developed, such as the new non-steroidal drug felbinac and the highly effective antihypertensive drug aminoamide. Nitrophenylacetic acid can also form luminescent materials with rare earth metals with good properties, so it has a wide range of applications in rare earth functional materials. It can be seen that nitrophenylacetic acid is a very important organic chemical product, and it is very urgent to develop its clean production process when environmental pollution has become a global problem of general concern. [0003] The relatively mat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/56
Inventor 李文英田青平冯杰谢克昌
Owner TAIYUAN UNIV OF TECH
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