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A kind of preparation method of 2-cyclopropyl propionaldehyde

A technology of cyclopropyl propanal and cyclopropyl methyl ketone, which is applied in the field of preparation of 2-cyclopropyl propanal, can solve the problems of high yield and few steps, achieve high yield, few by-products, low cost effect

Active Publication Date: 2020-08-21
HUAIAN GUORUI CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The method for synthesizing 2-cyclopropyl propionaldehyde in CN102584558A has few steps and high yield, but uses carcinogen dimethyl sulfate and low-boiling dimethyl sulfide

Method used

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  • A kind of preparation method of 2-cyclopropyl propionaldehyde
  • A kind of preparation method of 2-cyclopropyl propionaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 317.93g (1.2mol) of triphenylphosphine, 251.56g (3.24mol) of methylal and 3.1g of methanol into a four-neck flask, add 118.94g (1.5mol) of acetyl chloride dropwise at room temperature, dropwise for 4 hours, dropwise After completion, the temperature was raised to 50° C. and refluxed for 4 hours; filtered, the filter cake was rinsed with 100 g of toluene, and the filter cake was dried to obtain 406.3 g of methoxymethyltriphenylphosphorous chloride, with a yield of 98.8%.

[0023] Add 41.59g (0.12mol) of methoxymethyltriphenylphosphorous chloride and 150g of tetrahydrofuran into a four-necked flask, cool down to 0°C, add 13.6g (0.12mol) of potassium tert-butoxide in batches, and then dropwise add Cyclopropyl methyl ketone 8.5g (0.1mol), dropwise time is 0.5h, dropwise temperature is 15°C, after the dropwise addition is completed, react at 25°C for 0.5h; remove 75g of tetrahydrofuran under normal pressure, add 58.4g of hydrochloric acid (wt15 %, 0.24mol), the temperatu...

Embodiment 2

[0025] Add 317.93g (1.2mol) of triphenylphosphine, 232.9g (3mol) of methylal and 3.8g of methanol into a four-neck flask, add 87.2g (1.1mol) of acetyl chloride dropwise at room temperature, dropwise for 3 hours, and end the dropwise addition Afterwards, the temperature was raised to 50° C. and refluxed for 3 hours; filtered, the filter cake was rinsed with 100 g of toluene, and the filter cake was dried to obtain 394 g of methoxymethyltriphenylphosphorous chloride, with a yield of 95.8%.

[0026] Add 69.3g (0.2mol) of methoxymethyltriphenylphosphonium chloride and 200g of tetrahydrofuran into a four-necked flask, cool down to -10°C, add 27.2g (0.24mol) of potassium tert-butoxide in batches, and drop Add 11.33g (0.133mol) of cyclopropyl methyl ketone, dropwise time is 1h, dropwise temperature is 20°C, after the dropwise addition is completed, react at 30°C for 2h; remove 150g THF under normal pressure, add 129.36g sulfuric acid (wt20% , 0.264mol), the temperature was raised to ...

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Abstract

The invention relates to the field of organic synthesis, in particular to a synthesis method of 2-cyclopropyl propanal. According to the method, methoxy methyl triphenyl phosphonium chloride is reacted with cyclopropyl methyl ketone under the action of a base to generate 1-methoxy-2-cyclopropyl propanal; and the 1-methoxy-2-cyclopropyl propanal undergoes acidification and hydrolysis form the 2-cyclopropyl propanal. The synthesized 2-cyclopropyl propanal is calculated by cyclopropyl methyl ketone, has a yield which is more than 95%, and has the advantages of being less in by-products, high in yield and low in cost.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of 2-cyclopropyl propanal. Background technique [0002] 1-(4-Chlorophenyl)-2-cyclopropyl-1-propanone is an important intermediate for the synthesis of triazole low-toxicity and high-efficiency fungicide cyproconazole. CN102584558A proposes to use cyclopropyl methyl ketone as raw material, through Sulfur ylide reaction and catalytic rearrangement to synthesize 2-cyclopropylpropionaldehyde; 2-cyclopropylpropionaldehyde is oxidized and then reacted with thionyl chloride to obtain 2-cyclopropylpropionyl chloride; 2-cyclopropylpropionyl chloride and Chlorobenzene, anhydrous aluminum oxide reaction obtains 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone; CN105152886 takes 2-cyclopropyl propanal as raw material, reacts with hydroxylamine hydrochloride to obtain cyclopropyl Acetaldehyde oxime, then reacts with p-chlorophenyl diazonium salt to obtain 1-(4-chlorophenyl)...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/51C07C47/11
CPCC07C41/01C07C45/513C07C2601/02C07C47/11C07C43/162
Inventor 李明张璞陈超王凤云钟钰陈明光毛更生
Owner HUAIAN GUORUI CHEM CO LTD
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