Process for synthesizing 6-ethyl mercapto-3-heptylene-2-ketone

A synthesis method and ethylthio-based technology are applied in the preparation of thioethers, organic chemistry, etc., and can solve the problems of complicated operation, expensive post-processing, and many steps, and achieve the effects of good atom economy, low cost, and simplified steps.

Active Publication Date: 2011-05-25
BC P INC CHINA NAT PETROLEUM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first method needs to control the pH value, and the operation is cumbersome; the second method needs to use expensive witting reagents and the post-processing is difficult; the third method obviously has more steps compared with the present invention, waste of raw materials, and higher cost.

Method used

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  • Process for synthesizing 6-ethyl mercapto-3-heptylene-2-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Sodium hydroxide catalyzed the synthesis of 6-ethylthio-3-hepten-2-one.

[0012] Mix 15ml of acetone (0.2mol, 11.6g) and 45ml of 1.5% aqueous sodium hydroxide solution (wherein the quality of sodium hydroxide is 0.68g, 0.017mol) and place in a thermometer, reflux condenser, constant pressure dropping funnel In a 100ml three-necked flask, stir to make it evenly mixed, and heat to make it boil. In boiling state, slowly drop into the mixture of 3.90g of 3-ethylthiobutyraldehyde (0.03mol) and 10ml of acetone (0.13mol, 7.54g). Control the rate of addition, and the dropwise addition is completed in 2 hours. During the dropwise addition, the temperature is controlled so that the system is always in a boiling state. After the dropwise addition, the system was kept in a boiling state and reacted for 3 hours. The components of the TLC detection system no longer changed. The layers were separated, and the aqueous phase (lower layer) was washed with 3×10 ml of dichloromethane, a...

Embodiment 2

[0014] Sodium carbonate catalyzed the synthesis of 6-ethylthio-3-hepten-2-one.

[0015] 15ml of acetone (0.2mol, 11.6g) and 20ml of 5% sodium carbonate aqueous solution (wherein the quality of sodium carbonate is 1.00g, 0.009mol) are mixed and placed in a 100ml three-necked thermometer equipped with a reflux condenser and a constant pressure dropping funnel. In the flask, stir to mix well and heat to boil. In boiling state, slowly drop into the mixture of 3.90g of 3-ethylthiobutyraldehyde (0.03mol) and 10ml of acetone (0.13mol, 7.54g). Control the rate of addition, and the dropwise addition is completed in 2 hours. During the dropwise addition, the temperature is controlled so that the system is always in a boiling state. After the dropwise addition, the system was kept in a boiling state and reacted for 3 hours. The components of the TLC detection system no longer changed. The system was extracted with 3×10 ml of dichloromethane, and the organic phases (lower layer) were c...

Embodiment 3

[0017] Synthesis of 6-ethylthio-3-hepten-2-one catalyzed by low temperature potassium hydroxide.

[0018] Mix 15ml of acetone (0.2mol, 11.6g) and 4.5ml of 15% aqueous sodium hydroxide solution (wherein the quality of sodium hydroxide is 0.78g, 0.02mol) and place in a container equipped with a thermometer, a reflux condenser, and a constant pressure dropping funnel. In a 100ml three-necked flask, stir to make it evenly mixed, and cool to 15°C. At this temperature, slowly drop in a mixture of 3.90g 3-ethylthiobutyraldehyde (0.03mol) and 10ml acetone (0.13mol, 7.54g), and control The rate of addition was completed in 2 hours. Extract with 3×10ml dichloromethane, and combine the organic phases. Anhydrous sodium sulfate was dried overnight, and the solvent was evaporated under reduced pressure to obtain a mixture of crude product 6-ethylthio-3-hepten-2-one and 6-ethylthio-4-hydroxyl-2-heptanone, of which 6 -Ethylthio-4-hydroxy-2-heptanone as the main product.

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Abstract

The invention relates to a method for synthesizing 6-ethylthio-3-heptene-2-ketone. The method comprises the following steps of: mixing a dilute alkali solution with a concentration of between 1 and 20 percent and acetone, and heating the mixture to 60 DEG C; slowly adding 3-ethylthio butyraldehyde into the mixture for 0.5 to 10 hours, with a mol ratio of a solute in the dilute alkali solution to the 3-ethylthio butyraldehyde being 0.3-1.5 to 1, a pH value being between 9 and 11, and the quality of the acetone being 0.44 to 8.8 times of that of the 3-ethylthio butyraldehyde; constantly maintaining a boiling state of the system during the process of dripping the 3-ethylthio butyraldehyde; and maintaining the system below 60 DEG C after dripping is completed, and stirring for 2 hours to obtain the 6-ethylthio-3-heptene-2-ketone. In the reaction, the acetone is substituted for sodium acetoacetate to directly react with the 3-ethylthio butyraldehyde under an alkali condition, and dehydration can be directly realized under the condition, thereby realizing one-step synthesis of a product. The method has the advantages of simplified steps, low cost, good atom economy, greenness and environmental friendliness.

Description

Technical field: [0001] The present invention relates to a kind of synthetic method that uses acetone as raw material to directly convert 3-ethylthiobutyraldehyde into 6-ethylthio-3-hepten-2-one under alkaline conditions, and its target compound can be used for herbicidal activity Synthesis of compounds. Background technique: [0002] 6-Ethylthio-3-hepten-2-one is an important pesticide and pharmaceutical intermediate, which is widely used in the synthesis of cyclohexenone herbicides. The synthesis of the target compound 6-ethylthio-3-hepten-2-one is rarely reported in China, and foreign reports mainly contain three methods: (1) According to the report of U.S. Patent USP6300281, ethyl acetoacetate is used in aqueous sodium hydroxide solution Sodium acetoacetate is obtained by hydrolysis, then reacted with 3-ethylthiobutyraldehyde, and finally obtained by dehydration; (2) prepared by witting reaction, that is, triphenylphosphine-2-propanone and 3-ethylthio Butyraldehyde rea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/22C07C319/20
Inventor 张锁秦霍凤华徐昊田洋张广良刘纯宜郑良玉田晓军李耀先
Owner BC P INC CHINA NAT PETROLEUM CORP
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