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A kind of synthetic method of ester compound

The technology of an ester compound and a synthesis method, which is applied in the synthesis field of the ester compound, can solve the problems of waste of resources, environment, pollution, etc., and achieves the effects of short reaction time, broad application prospects, and cheap and easily available raw materials

Active Publication Date: 2018-08-10
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of the first method is: since the condensation reaction is reversible, it is necessary to use a large excess of reactant or dehydrating agent to promote the effective carrying out of the reaction; the disadvantage of the second method is that: the high activity used Carboxylic acid derivatives need to be prepared from carboxylic acid, and the corresponding preparation reaction must be completed under harsh reaction conditions, accompanied by the generation of a large number of by-products, resulting in waste of resources and environmental pollution

Method used

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  • A kind of synthetic method of ester compound
  • A kind of synthetic method of ester compound
  • A kind of synthetic method of ester compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011]

[0012] Add p-methoxybenzaldehyde (1a, 0.5mmol, 68mg), bromo-n-butane (2a, 1mmol, 137mg), water (2mL), tert-butyl hydroperoxide (1mmol, 138μL) into a 25mL pressure-resistant tube , 70wt% aqueous solution) and tetrabutylammonium iodide (0.5mmol, 184mg), then the pressure tube was sealed and placed in an oil bath, and stirred at 80°C for 2 hours. After the reaction was completed, 10 mL of water was added, extracted with ethyl acetate (10 mL×3), the combined organic phases were washed with Na 2 S 2 o 3 Washed with aqueous solution, then dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the product was separated on a silica gel column (petroleum ether / ethyl acetate=30 / 1) to obtain the product 3a (75 mg, 72%) as a colorless oil. The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 )δ: 0.89(t, J=7.2Hz, 3H), 1.34-1.43(m, 2H), 1.62-1.69(m, 2H), 3.77(s, 3H), 4.21(t, J=6.8Hz, 2H ),6.81-6.85(m,2...

Embodiment 2

[0014] Add p-methoxybenzaldehyde (1a, 0.5mmol, 68mg), bromo-n-butane (2a, 1mmol, 137mg), acetonitrile (2mL), tert-butyl hydroperoxide (0.5mmol, 69μL, 70wt% aqueous solution) and tetrabutylammonium iodide (0.1mmol, 37mg), then the pressure tube was sealed and placed in an oil bath, and stirred at 80°C for 2 hours. After the reaction was completed, 10 mL of water was added, extracted with ethyl acetate (10 mL×3), the combined organic phases were washed with Na 2 S 2 o 3 Washed with aqueous solution, then dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the product was separated on a silica gel column (petroleum ether / ethyl acetate=30 / 1) to obtain the product 3a (23 mg, 22%) as a colorless oil.

Embodiment 3

[0016] Add p-methoxybenzaldehyde (1a, 0.5mmol, 68mg), bromo-n-butane (2a, 1mmol, 137mg), acetonitrile (2mL), tert-butyl hydroperoxide (1mmol, 138μL) into a 25mL pressure tube , 70wt% aqueous solution) and tetrabutylammonium iodide (0.1mmol, 37mg), then the pressure tube was sealed and placed in an oil bath, and stirred at 80°C for 2 hours. After the reaction was completed, 10 mL of water was added, extracted with ethyl acetate (10 mL×3), the combined organic phases were washed with Na 2 S 2 o 3 Washed with aqueous solution, then dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the product was separated on a silica gel column (petroleum ether / ethyl acetate=30 / 1) to obtain the product 3a (33 mg, 32%) as a colorless oil.

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Abstract

The invention discloses a synthetic method of an ester compound and belongs to the technical field of organic synthesis. The synthetic method includes the steps of: dissolving an aldehyde compound (1) and a halogenated hydrocarbon compound (2) in a solvent, adding an oxidant and a catalyst, and performing a reaction at 60-100 DEG C to obtain the target product ester compound (3). A reaction equation of the synthetic method is represented as follows. The method, compared with the prior art, has the following advantages: 1) the raw materials are easy to obtain and are low in cost; 2) the reaction conditions are mild, operations are simple, and reaction time is short; and 3) a substrate has wide available range and can be used for synthesis of various ester compounds.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing ester compounds. Background technique [0002] Esters are one of the most important organic compounds. They not only widely exist in various natural products, but also have good biological activity. On the other hand, esters have rich reactivity and can be used as intermediates in the synthesis of various functional organic molecules. At present, there are two main synthetic methods of ester compounds, one is to complete through the condensation reaction between carboxylic acid and alcohol, and the other is to complete through the affinity reaction between alcohol and carboxylic acid derivatives (such as acid halide or acid anhydride, etc.). nuclear substitution reaction. The disadvantage of the first method is: since the condensation reaction is reversible, it is necessary to use a large excess of reactant or dehydrating agent to...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/44C07C69/92C07C69/78C07C69/76C07C69/618C07C69/24C07C201/12C07C205/57C07C253/30C07C255/57C07D333/40C07D307/68C07D213/807C07B41/12
CPCC07B41/12C07C67/44C07C201/12C07C253/30C07D213/807C07D307/68C07D333/40C07C69/92C07C69/78C07C69/76C07C69/618C07C69/24C07C205/57C07C255/57
Inventor 张新迎王倩倩范学森王章欣徐园双
Owner HENAN NORMAL UNIV
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