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Method for preparing para methoxy phenyl acetonitrile

A technology of methoxybenzene acetonitrile and p-methoxybenzene, which is applied in the synthesis of pharmaceutical intermediates and the synthesis of nitriles from aldehydes, can solve problems such as poor operability and yield, and achieve improved total yield and simplified process. , the effect of reducing costs

Inactive Publication Date: 2010-07-14
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the raw material is cheaper than p-methoxybenzaldehyde, the operability and yield of the reaction are much worse than the indirect method

Method used

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  • Method for preparing para methoxy phenyl acetonitrile
  • Method for preparing para methoxy phenyl acetonitrile

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0015] Example 1: the preparation of p-methoxyphenylacetonitrile:

[0016] The preparation of step a p-methoxybenzyl alcohol:

[0017] Take 136g (1mol) of p-methoxybenzaldehyde and add it to a 500ml three-necked flask, control the temperature at 10-40°C, dissolve 19g (0.35mol) of potassium borohydride in 50ml of water, add the potassium borohydride solution dropwise, and use TLC detection end point. After the reaction was completed, 200ml of dichloromethane was added to separate the layers, and the aqueous layer was extracted once with 100ml of dichloromethane, and the organic phases were combined. After the organic phase was dried by adding anhydrous sodium sulfate, it was directly put into the next step reaction, GC>99%.

[0018] Step b: the preparation of p-methoxybenzyl chloride:

[0019] The above organic phase was added into a 1000ml three-neck flask, the reaction temperature was controlled between 20°C and 50°C, 131g (1.1mol) of thionyl chloride was added dropwise, a...

example 2

[0022] Example 2: the preparation of p-methoxyphenylacetonitrile:

[0023] The preparation of step a p-methoxybenzyl alcohol:

[0024] Take 136g (1mol) of p-methoxybenzaldehyde and add it to a 500ml three-necked flask, control the temperature at 10-40°C, take 19g (0.35mol) of potassium borohydride and add it in batches, and control the reaction during the batch addition process. temperature. Then add 200ml of water, continue the reaction, and detect the end point by TLC. 200ml of dichloromethane was added for liquid separation, the aqueous layer was extracted once with 100ml of dichloromethane, and the organic phases were combined. After drying, the solvent was spin-dried to obtain 138 g of product, GC>99%.

[0025] Step b: the preparation of p-methoxybenzyl chloride:

[0026] Add the above product into a 1000ml three-neck flask, add 400ml of dichloromethane to dissolve, control the reaction temperature between 20 and 50°C, take 131g (1.1mol) of thionyl chloride and add it...

example 3

[0029] Example 3: the preparation of p-methoxyphenylacetonitrile:

[0030] Step a: the preparation of p-methoxybenzyl alcohol:

[0031] Take 136g (1mol) of p-methoxybenzaldehyde and add it to a 500ml three-necked flask, control the temperature at 10-40°C, take 13.2g (0.35mol) of sodium borohydride and dissolve it in 50ml of water, add the above solution dropwise, and continue the reaction , TLC detection endpoint. 200ml of dichloromethane was added for liquid separation, the aqueous layer was extracted with 100ml of dichloromethane, and the organic phases were combined. After drying, the solvent was spin-dried to obtain 138 g of product, GC>99%.

[0032] Step b: the preparation of p-methoxybenzyl chloride:

[0033] Add the product from the previous step into a 1000ml three-neck flask, add 400ml of dichloromethane to dissolve, control the reaction temperature between 20 and 50°C, take 131g (1.1mol) of thionyl chloride and drop it into the reaction flask, and control the drip...

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Abstract

The invention relates to a method for preparing para methoxy phenyl acetonitrile, which comprises the following steps: firstly adopting p-methoxybenzaldehyde as the raw material to generate anisyl alcohol under the action of a reducing agent; after drying the obtained reaction product, carrying out chlorination on the dried reaction product by thionyl chloride to obtain benzyl chloride; and carrying out cyanoethylation reaction on the obtained benzyl chloride under the alkaling conndition and under the action of a phase transfer catalyst to obtain the para methoxy phenyl acetonitrile, wherein the total yield of the para methoxy phenyl acetonitrile reaches over 85 percent.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to the technical field of synthesizing nitriles from aldehydes. Background technique [0002] P-methoxyphenylacetonitrile is mainly used in the synthesis of pharmaceuticals, pesticides and other chemical products, and is an important organic intermediate. There are many methods for the synthesis of p-methoxyphenylacetonitrile. It has been reported in the literature that p-methoxybenzaldehyde is directly used to synthesize p-methoxyphenylacetonitrile, Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), (11), 2635- 40; 1984 reported the direct synthesis with triphenylphosphine, but the yield in the literature was lower than 50%, Synthetic Communications, 10 (5), 399-403; 1980 reported the direct synthesis, but the yield reported in the literature was only 70%. Simultaneously document Tetrahedron Le...

Claims

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Application Information

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IPC IPC(8): C07C255/37C07C253/14B01J31/02
Inventor 杨兵赛达力木·伊吾热衣木江顾秀娟叶玲玲赵敏吴范宏肖时俊
Owner EAST CHINA UNIV OF SCI & TECH
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