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Synthesis method for ester compound

A technology of ether compound and synthesis method, which is applied in the field of synthesis of organic compounds and achieves the effects of high yield, strong substrate universality and mild reaction conditions

Inactive Publication Date: 2018-03-09
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to aim at the deficiencies and technical difficulties in the traditional preparation of ether compounds, to provide a method that does not involve a strong base and does not affect the reaction separation, the raw materials are readily available and no pretreatment is required, the reaction is simple and Method for synthesizing ether compounds with advantages such as strong functional group tolerance

Method used

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  • Synthesis method for ester compound
  • Synthesis method for ester compound
  • Synthesis method for ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] Add 0.3mmol of α-vinyl o-phenylbenzyl alcohol, 0.18mmol of potassium persulfate, and 0.6mmol of sodium trifluoromethanesulfonate into a 15mL pressure-resistant tube, and then add 2.4mL of 1,4-dioxane as a solvent. Next, magnetically stir at 45° C. for 12 h. Then, the reaction solution was cooled to room temperature, the filter residue was removed by filtration, and the filter residue was washed with dichloromethane, the filtrate was combined, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the filtrate, and the solvent was removed by distillation under reduced pressure. The residue was separated by column chromatography (petroleum ether: ethyl acetate volume ratio = 15:1 as the eluent), and the eluate containing the target product was collected, and the solvent was evaporated to obtain the pure product. The substance is a light yellow liquid, the chemical name is bis-(2-phenylphenyl)allyl ether, the amount of the purified subst...

Embodiment 2

[0029]

[0030] Add 0.3mmol of α-vinyl o-phenylbenzyl alcohol, 0.09mmol of potassium persulfate, and 0.9mmol of sodium trifluoromethanesulfonate into a 15mL pressure-resistant tube, and then add 1.5mL of 1,4-dioxane as a solvent. Then, magnetic stirring was performed at 25 °C for 8 h. Then, the reaction solution was cooled to room temperature, the filter residue was removed by filtration, and the filter residue was washed with dichloromethane, the filtrate was combined, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the filtrate, and the solvent was removed by distillation under reduced pressure. The residue was separated by column chromatography (petroleum ether: ethyl acetate volume ratio = 15:1 as the eluent), and the eluate containing the target product was collected, and the solvent was evaporated to obtain the pure product. The substance is a light yellow liquid, the chemical name is bis-(2-phenylphenyl)allyl ether, the amount of the pu...

Embodiment 3

[0033]

[0034] Add 0.3mmol of α-vinyl o-phenylbenzyl alcohol, 0.3mmol of potassium persulfate, and 0.9mmol of copper trifluoromethanesulfonate into a 15mL pressure-resistant tube, and then add 3.0mL of 1,4-dioxane as a solvent. Then, magnetically stirred at 80° C. for 24 h. Then, the reaction solution was cooled to room temperature, the filter residue was removed by filtration, and the filter residue was washed with dichloromethane, the filtrate was combined, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the filtrate, and the solvent was removed by distillation under reduced pressure. The residue was separated by column chromatography (petroleum ether: ethyl acetate volume ratio = 15:1 as the eluent), and the eluate containing the target product was collected, and the solvent was evaporated to obtain the pure product. The substance is a light yellow liquid, the chemical name is bis-(2-phenylphenyl)allyl ether, the amount of the purified sub...

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Abstract

The invention discloses a synthesis method for a bis(2-biphenyl) allyl ether compound. According to the synthesis method, a corresponding target product is prepared by taking an alpha-ethylene-o-phenylbenzyl alcohol compound as a raw material and reacting under the action of an oxidizing agent and BDPAT in an organic solvent. The synthesis method disclosed by the invention has the advantages thatstrong alkaline is not used, the operation is safe, the reaction conditions are mild, the synthesis method is environmentally friendly, waste gas and waste water are not produced in a reacting process, the operation is simple and convenient and the like.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing ether compounds. (2) Background technology [0002] In recent years, the biological activity of ether compounds has received great attention. Ether compounds have anti-tumor activity, anti-plant virus, herbicide, bactericidal, anti-inflammatory effects, and inhibit angiotensin-converting enzyme, aminopeptidase, HIV protease and other important biological activities. Therefore, ether compounds are widely used in the manufacture of pharmaceutical industry and are very important pharmaceutical intermediates. [0003] The synthetic methods of ether compounds reported in the literature mainly contain the following methods: (1) Williamson synthetic method (referring to Molecular Carginogenesis, 2004,40,201); (2) using quaternary ammonium salt as phase transfer catalyst synthetic method (referring to Tetrabedron, 1974, 30, 1382). But the fir...

Claims

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Application Information

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IPC IPC(8): C07C41/01C07C43/166C07C43/176C07C201/12C07C205/34
CPCC07C41/01C07C201/12C07C205/34C07C43/166C07C43/176
Inventor 刘运奎张海峰鲍汉扬
Owner ZHEJIANG UNIV OF TECH