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Synthetic method for olefin compounds

A synthetic method and compound technology, applied in organic chemical methods, chemical instruments and methods, and hydrocarbon production from oxygen-containing organic compounds, etc., can solve the problems of harsh reaction conditions, many side reactions, and long reaction time, and achieve simple operation, Mild reaction and low corrosion effect

Inactive Publication Date: 2013-12-04
SUZHOU RES INST LANZHOU INST OF CHEM PHYSICS CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to overcome the shortcomings of using transition metals and strong protonic acids or highly corrosive catalysts, harsh reaction conditions, long reaction times, and many side reactions in the prior art, and provide a Ionic liquid-catalyzed alkylation of alcohols with alcohols and olefins to generate olefins is a more efficient, economical and environmentally friendly method

Method used

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  • Synthetic method for olefin compounds
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  • Synthetic method for olefin compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0049]

[0050] At 80°C, put α-phenylethanol (1.0mmol, 122mg) and 4-chlorobenzhydryl alcohol (0.5mmol, 109.3mg) and [BsOdP]OTf (10mol%, 30.5mg), dichloromethane 2.0mL in a dry place In the reaction flask, magnetically stirred, and reacted for 12h. After the reaction, column chromatography separation (using silica gel column; eluent: petroleum ether) to obtain pure product: (E)-(3-(p-chlorophenyl)-1,3-diphenyl-1-propene , 121.6 mg, the yield was 80%.

Embodiment 2

[0052] At 80°C, α-phenylethanol (1.0mmol, 122mg) and 4-chlorobenzhydryl alcohol (0.5mmol, 109.3mg) and [BsMIm][HSO 4 ] (10mol%, 30.5mg), dichloromethane 2.0mL was placed in a dry reaction flask, magnetically stirred, and reacted for 12h. After the reaction, column chromatography separation (using silica gel column; eluent: petroleum ether) to obtain pure product: (E)-(3-(p-chlorophenyl)-1,3-diphenyl-1-propene , and the yield was 31%.

Embodiment 3

[0054] At 80°C, put α-phenylethanol (1.0mmol, 122mg) and 4-chlorobenzhydryl alcohol (0.5mmol, 109.3mg) and [BsMIm][OTf] (10mol%, 30.5mg), dichloromethane 2.0mL In a dry reaction vial, stirred by magnetic force, reacted for 12h. After the reaction, column chromatography separation (using silica gel column; eluent: petroleum ether) to obtain pure product: (E)-(3-(p-chlorophenyl)-1,3-diphenyl-1-propene , the yield is 55%.

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Abstract

The invention discloses a synthetic method for olefin compounds. According to the synthetic method, a functionalized ionic liquid is taken as a catalyst, and the reactants are catalyzed and subjected to an alkylation reaction for synthesis of the olefin compounds. The catalyst is an acid-functionalized ionic liquid belonging to a nonmetal system and is environment friendly; the catalyst is small in use amount, high in catalytic activity, good in stability and low in corrosivity; the synthetic method has good product selectivity, simple operation, strong controllability, wide substrate application scope, mild reaction condition, simple post treatment and easy separability between the products and the catalyst; and the catalyst is reusable.

Description

technical field [0001] The invention relates to a method for synthesizing olefinic compounds. Background technique [0002] The construction of C-C bonds is one of the important research contents in the field of organic synthesis, and has important application value in theoretical research and industrial and agricultural production. Alkylation of alcohols is an important method for constructing C-C bonds. Olefin compounds synthesized by this method are important chemical raw materials and have important uses in organic synthesis, pharmaceuticals, polymer materials and fine product chemistry. The synthesis method of olefins commonly used in the industry comes from the cracking of petroleum. The polymerized olefins can be used to synthesize resins, fibers, plastics, etc., and have good physical and chemical properties, such as: good electrical insulation performance, chemical corrosion resistance , cold resistance, non-toxic, can be made into film as packaging material for fo...

Claims

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Application Information

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IPC IPC(8): C07B37/00C07C25/28C07C17/26C07C15/50C07C15/58C07C1/20
Inventor 陈静杨磊韩峰李臻夏春谷
Owner SUZHOU RES INST LANZHOU INST OF CHEM PHYSICS CHINESE ACADEMY OF SCI
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