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A green and efficient synthesis method of ether compounds

A technology of ether compounds and synthetic methods, which is applied in ether preparation, organic chemistry, etc., can solve the problems of easy elimination of tertiary alcohol reaction, low yield of secondary alcohol reaction, high reaction temperature, etc., and achieve the effect of good industrial application prospect

Active Publication Date: 2021-02-12
XUZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction temperature of this method is relatively high, the post-treatment is complicated, and a stoichiometric copper salt catalyst is required, and the conversion rate is low.
[0005] (3) The dehydration reaction of alcohol, which is a common method for synthesizing symmetrical ethers, but this method is mainly used for the reaction of primary alcohols into ethers, the reaction yield of secondary alcohols is relatively low, and the reaction of tertiary alcohols is easy to eliminate
However, this type of method requires the use of a large amount of organic solvents, and post-treatment requires cumbersome purification methods such as column chromatography
[0007] In summary, in the existing methods for synthesizing ethers, either the reaction conditions require the use of strong acids and strong bases, or the temperature required for the reaction is higher, or the required reagents are expensive, or the post-treatment is cumbersome.
The particularly prominent problem is that the existing method uses a high amount of catalyst, which pollutes the environment, and the post-treatment process must be purified by column chromatography, which is time-consuming and consumable.

Method used

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  • A green and efficient synthesis method of ether compounds
  • A green and efficient synthesis method of ether compounds
  • A green and efficient synthesis method of ether compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: 100mL round-bottomed flask is added successively with 0.02% AgNTf 2 (0.01mmol, 3.88mg), benzaldehyde (50mmol, 5.3060g) and triethylsilane (50mmol, 6.0600g), the reaction mixture was heated to 80 ° C, stirred for 70 minutes (the corresponding reaction mechanism can refer to figure 1 ), and direct vacuum distillation (2mmHg, 90°C) to obtain the target product with a yield of 97%. The structural characterization data of the product dibenzyl ether are consistent with the literature (Gellert, Beate A.; Kahlcke, Nils; Feurer, Markus. Chemistry-A European Journal, 2011, 17, 43, 12203-12209): 1 H NMR (400MH Z , CDCl 3 ): δppm7.31-7.40 (m, 10H), 4.58 (s, 4H); 13 C NMR (100MH Z , CDCl 3 ): δppm 138.2, 128.4, 127.8, 127.6, 72.1; IR (cm -1 ):3050,1420,1380; ESI + calculated for [C 14 h 15 O] + :199.2730,found:199.2727.

Embodiment 2

[0044] Embodiment 2: first add 100ppmAgOAc (0.005mmol, 8mg) in the round bottom flask of 1000mL, benzaldehyde (500mmol, 53.0600g) and triethylsilane (500mmol, 60.6000g), be heated to 110 ℃, stir reaction 3h, react After completion, direct vacuum distillation (2mmHg, 90°C) gave the target product with a yield of 92%. Product structure characterization data are the same as in Example 1.

Embodiment 3

[0045] Embodiment 3: Add 0.1% AgNTf in sequence in 1000mL reaction bottle 2 (0.5mmol, 0.2g), benzaldehyde (500mmol, 53.06g) and triethylsilane (500mmol, 60.60g), stirred and reacted at room temperature at 25°C for 2h, after the reaction was completed, 50ml of water was added to the reaction flask, and the liquid was separated , the organic phase was dried with anhydrous sodium sulfate, and then the organic phase was distilled under reduced pressure (2 mmHg, 90° C.) to obtain the target product with a yield of 86%. Product structure characterization data are the same as in Example 1.

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Abstract

The invention discloses a green and high-efficiency synthesis method of ether compounds, which is energy-saving and environment-friendly. , through the reduction-coupling-ether formation reaction, the efficient preparation of various ethers is realized. The synthesis method of the present invention has the advantages of low catalyst consumption, no solvent, high conversion rate and yield, short reaction time, safety and stability, easy operation, product only needs to be purified by distillation without any additional organic solvent, whole process is green, environmental protection, high efficiency, etc. , can overcome many defects of the prior art, and has good industrial application value.

Description

technical field [0001] The invention relates to a synthesis method of ether compounds, in particular to a green and efficient synthesis method of symmetrical ether compounds, belonging to the technical field of organic synthesis. Background technique [0002] Ether is a very important compound, which plays a very important role in organic synthesis and drug synthesis, and is also an important class of industrial raw materials. It is the focus of attention of organic chemists to find a simple, efficient and environmentally friendly synthesis method of ether. (Angew.Chem.Int.Ed., 2007, 46, 298-300.) At present, there are many preparation methods for ether compounds, but there are generally defects such as complex synthesis process and relatively large pollution to the environment. Existing ether synthetic method mainly contains following several kinds: [0003] (1) The Williamson synthesis method, comprising: using halogenated hydrocarbons, sodium alkoxide and sodium phenate ...

Claims

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Application Information

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IPC IPC(8): C07D309/04C07D307/87C07C41/01C07C43/04C07C43/164C07C43/174
CPCC07C41/01C07D307/87C07D309/04C07C43/04C07C43/164C07C43/1742
Inventor 徐洲梁婷米佳佳翟荣良石艳芬
Owner XUZHOU MEDICAL UNIV