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Synthesis method of 2,3-dihydrobenzofuran

A synthesis method and technology of dihydrobenzene, applied in the direction of organic chemistry, etc., can solve the problems of many reaction by-products, reduced yield and product quality, and low yield, and achieve the goal of increasing yield, reducing energy consumption, and optimizing the reaction process Effect

Active Publication Date: 2016-06-22
ITIC MEDCHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method is comparatively easy, is the closest prior art of the present invention, but this method productive rate is lower, and the reaction by-product of this type of reaction is more simultaneously, and the C-O bond in 2-phenoxyethanol will be broken when the temperature is too high A large amount of phenol or other by-products are produced. If the temperature is too low, it is not conducive to the occurrence of the reaction. Therefore, the temperature control is very strict, and a little careless temperature control will cause a sharp decrease in output and product quality.

Method used

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  • Synthesis method of 2,3-dihydrobenzofuran
  • Synthesis method of 2,3-dihydrobenzofuran

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preparation example Construction

[0033] The preparation method of the catalyst is as follows: mixing cupric chloride and ferric chloride according to mass ratio, pressing into tablets, drying at 150-200 DEG C and calcining at 500-550 DEG C to obtain it.

[0034] The effect of the solid mass addition of copper chloride and ferric chloride mixed solid catalyst on the yield of 2-phenoxyethanol was tested, and the results are shown in Table 1.

[0035] Table 1: The effect of copper chloride and ferric chloride solid addition quality on the yield of 2-phenoxyethanol

[0036] Experiment number 1 2 3 4 5 6 7 8 9 Copper chloride (g) 30 0 15 22.5 25 26.3 7.5 5 26.3 Ferric chloride (g) 0 30 15 7.5 5 3.7 22.5 25 3.7 Yield(%) 80 78 79 92 90 82 85 84 83

[0037] When the mass ratio of copper chloride to ferric chloride is 3:1-5:1, the yield of 2-phenoxyethanol is significantly improved.

[0038] The solid mass ratio of copper chloride and ferric chloride was...

Embodiment 1

[0051] A kind of synthetic method of 2,3-dihydrobenzofuran, comprises the following steps:

[0052] The first step: Synthesis of 2-phenoxyethanol:

[0053] Add 100ml of sodium phenate aqueous solution 100ml, 2-chloroethanol 67.1ml, cupric chloride and ferric chloride mixed solid 17.05g (the mass ratio of cupric chloride and ferric chloride is 3:1) in the 500ml container, heat Start timed reflux reaction at 60°C for 2 hours, cool to room temperature after the reaction to collect the organic layer, wash the organic layer twice with 3% aqueous sodium hydroxide solution to obtain 2-phenoxyethanol;

[0054] The second step: Synthesis of 2,3-dihydrobenzofuran:

[0055] Add the 2-phenoxyethanol synthesized in the first step above, 1 g of zinc chloride solid, and 3 g of manganese dichloride solid in a 250 ml container, mix and stir and heat to 200 ° C to start timing and reflux reaction for 3 hours. After the timing is over, slowly Cool down to room temperature, add 3% sodium hydrox...

Embodiment 2

[0057] A kind of synthetic method of 2,3-dihydrobenzofuran, comprises the following steps:

[0058] The first step: Synthesis of 2-phenoxyethanol:

[0059] Add 100ml of sodium phenate aqueous solution 100ml, 2-chloroethanol 100.65ml, cupric chloride and ferric chloride mixed solid 34.10g (the mass ratio of cupric chloride and ferric chloride is 5:1) in the 500ml container, heating Start timed reflux reaction at 70°C for 3 hours, cool to room temperature after the reaction to collect the organic layer, wash the organic layer with 5% aqueous sodium hydroxide solution for 3 times to obtain 2-phenoxyethanol;

[0060] The second step: Synthesis of 2,3-dihydrobenzofuran:

[0061] Add the 2-phenoxyethanol synthesized in the first step above, 1g of zinc chloride solid, and 5g of manganese dichloride solid into a 250ml container, mix and stir and heat to 220°C to start timed reflux reaction for 4 hours. Cool down to room temperature, add 5% sodium hydroxide aqueous solution to wash 3...

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Abstract

The invention discloses a synthesis method of 2,3-dihydrobenzofuran and belongs to the field of organic chemical synthesis. The preparation method comprises the steps that sodium phenate and 2-chloroethanol are used as raw materials, copper chloride and ferric chloride mixed solid is added as a catalyst, cooling is carried out after mixing, backflow and reflux reaction, an organic layer is collected, a sodium hydroxide solution is used for washing, 2-phenoxy ethanol is obtained, the 2-phenoxy ethanol is mixed with zinc chloride, manganous chloride is added as a catalyst, heating and reflux reaction are carried out, the sodium hydroxide solution is added for washing, reduced pressure distillation is carried out, fraction at the temperature of 88-90 DEG C is collected, and the 2,3-dihydrobenzofuran is obtained. According to the method, the copper chloride and ferric chloride mixture and the manganous chloride are used as the catalysts, the reaction technology and the reaction condition are optimized, the reaction temperature can be effectively decreased, reaction time can be shortened, the produced reaction by-products can be reduced, reaction efficiency can be improved, and the high economic benefit is obtained.

Description

Technical field: [0001] The invention relates to a synthesis method of 2,3-dihydrobenzofuran, which belongs to the field of chemical synthesis. Background technique: [0002] 2,3-Dihydrobenzofuran is a fine chemical raw material widely used in the synthesis of tricyclic compounds, and it is also an important pharmaceutical intermediate discovered in recent years, such as the anti-tumor agent benzofuransulfonyl Urinary compounds, HIV protease inhibitor amino acid aminosulfonphthalein, matrix metalloproteinase inhibitor arylsulfinamide hydroxamic acid, etc., so 2,3-dihydrobenzofuran is used as a pharmaceutical intermediate in the world There is a large market potential in the world, but the domestic production of such compounds is still relatively small. [0003] In the process of the synthesis of benzofuran, people have also made in-depth research on a large number of metal catalysts, mainly including transition metals such as palladium, copper, platinum, ruthenium, germaniu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/79
CPCC07D307/79
Inventor 胡海威丁靓闫永平郑辉严辉
Owner ITIC MEDCHEM CO LTD
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