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Cyclic carbonate compound and synthesis method thereof

A cyclocarbonate and compound technology, applied in the field of cyclocarbonate and its preparation, can solve problems such as high reaction temperature and long reaction time

Inactive Publication Date: 2013-01-23
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] Although cyclic carbonates can be obtained by the above methods, the above reactions all require catalysts, and there are long reaction times, high reaction temperatures, and the need for high-pressure carbon dioxide, so there are problems related to safe operation and the like.

Method used

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  • Cyclic carbonate compound and synthesis method thereof
  • Cyclic carbonate compound and synthesis method thereof
  • Cyclic carbonate compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] In a 25ml three-necked flask, benzaldehyde (2mmol, 0.212g) and α-bromoacetophenone (4mmol, 0.796g) were dissolved in anhydrous dioxane solution (5ml), stirred under a magnetic sub and 35 Under the water bath temperature of ℃, pass through the carbon dioxide gas flow under normal pressure (flow rate: 200-300ml / min), then LDA (2.5ml, 1M) is dripped into the above solution through the constant pressure funnel (the dripping process takes 2.5min ), and then the reaction system was reacted for ten minutes at a water bath temperature of 35° C. and a stable carbon dioxide gas flow condition. After the reaction was completed, the reaction was quenched by saturated ammonium chloride solution, extracted with ethyl acetate (10ml×3), dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel (100-200 mesh) column chromatography to obtain the target product-cyclocarbonate-4-phenyl-5-benzoyl-1,3-dioxol-2-one. Chro...

Embodiment 2

[0036] In the same apparatus as used in Example 1, under the same conditions, except that benzaldehyde was changed to p-methoxybenzaldehyde (0.272 g). 0.137 g of cyclocarbonate-4-(4'-methoxyphenyl)-5-benzoyl-1,3-dioxolan-2-one was obtained, the yield was 23%, and the product structure 9 was obtained.

[0037]

[0038] Formula 9

Embodiment 3

[0040] In the same apparatus as used in Example 1, under the same conditions, except that benzaldehyde was changed to o-methoxybenzaldehyde (0.272 g). Obtain 0.482g of cyclocarbonate-4-(2'-methoxyphenyl)-5-benzoyl-1,3-dioxol-2-one, the yield is 81%, and the product structure is as follows: 10.

[0041]

[0042] Formula 10

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Abstract

The invention discloses a cyclic carbonate and a preparation method thereof. The formula of the cyclic carbonate related by the invention is disclosed in the specification. The preparation method comprises the following steps: dissolving benzaldehyde or derivatives thereof and alpha-bromoacetophenone or derivatives thereof in an anhydrous dioxane solution; introducing carbon dioxide gas at the flow rate of 200-300 ml / min under atmospheric pressure at 10-55 DEG C while stirring; dropwisely adding diisopropyl lithium amide into the solution; leading the reaction system completely to react underthe conditions of stable carbon dioxide gas flow; and after the reaction finishes, quenching the reaction with saturated ammonium chloride solution, extracting with ethyl acetate, drying to remove the solvent, and carrying out silicagel column chromatography to obtain the target product.

Description

technical field [0001] The invention relates to a cyclocarbonate and a preparation method thereof. Background technique [0002] Cyclic carbonates are a class of compounds that are widely used in the field of chemical applications. They can be used as polar aprotic solvents and synthetic precursors of polycarbonate polymer compounds, as well as intermediates in organic synthesis. There are several methods for preparing cyclic carbonates: [0003] Synthesis of cyclic carbonates by oxidation from alkenes, see M.Aresta, A.Dibenedetto, I.Tommasi.Appl.Organomet.Chem., 2000, 14, 799-802.; N.Eghbali, C.J.Li.Green Chem., 2007, 9, 213-215.; J.L.Wang, J.Q.Wang, L.N.He, X.Y.Dou, F.Wu. Green Chem. 2008, 10, 1218-1223.; , 39-41., the reaction is as formula 1. [0004] [0005] Formula 1 [0006] Synthesis of cyclocarbonates starting from diols, see Y.Du, D.L.Kong, H.Y.Wang, F.Cai, H.S.Tian, ​​J.Q.Wang, L.N.He.J.Mol.Catal.A:Chem., 2005, 241, 233- 237.; S.Y.Huang, S.G.Liu, J.P.Li,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/36C07D407/04C07D405/04C07D409/04
Inventor 景欢旺闫鹏
Owner LANZHOU UNIVERSITY
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