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A kind of preparation method of ɑ, β-unsaturated ketone

An unsaturated and acetone technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry methods, etc., can solve the problem of intractable solid and strong alkaline waste, not in line with the spirit of green chemistry, and restricting large-scale production applications, etc. The problem is to achieve the effect of simple synthesis method, high yield and mild reaction conditions.

Active Publication Date: 2018-10-26
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, about α, β - There have been many reports in the literature on the research methods of unsaturated ketones, and in these methods, alkaline catalysts and organic solvents are mostly used. The catalysts and solvents used in these methods are harmful to the environment and will cause corrosion to equipment in industrial production , and the solid strong alkaline waste produced after the reaction is also difficult to deal with. These shortcomings limit its large-scale production and application in industry, and it does not conform to the spirit of green chemistry.

Method used

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  • A kind of preparation method of ɑ, β-unsaturated ketone
  • A kind of preparation method of ɑ, β-unsaturated ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] In a 15mL high-pressure sealed tube, add immobilized proline and 2,6-dimethylpiperazine, dissolve benzaldehyde in 1 mL of acetone, and add this mixed solution into the high-pressure sealed tube under nitrogen protection at 50 Under the condition of ℃, stir for 48 hours (the feeding amount is shown in Table 1), the reaction solution gradually turns light yellow. After the reaction, petroleum ether was added to the reaction solution until no precipitate was precipitated, filtered, washed with petroleum ether, and dried to obtain a solid catalyst for next use. The filtrate was separated and purified by thin-layer chromatography (developing solvent: petroleum ether and ethyl acetate mixed at a volume ratio of 10:1) or purified by column chromatography to obtain the final product - ɑ, β-unsaturated ketone, with a yield of 81.2% .

[0013] substance

molecular weight

millimoles

Mass / g

Benzaldehyde

106

1

0.1060

acetone

58

3

...

Embodiment 2

[0016] Embodiment 2: other conditions are the same as embodiment 1, and the reaction is checked under different temperatures, and the experimental results are shown in Table 2.

[0017] Numbering

[0018] It can be seen from the above table that the reaction temperature is the best under the condition of 50° C., and the yield is the highest.

Embodiment 3

[0019] Embodiment 3: other conditions are the same as embodiment 1, and the reaction under different co-catalyst conditions is checked, and the experimental results are shown in Table 3.

[0020] Table 3: Comparison table of the influence of different cocatalysts on the reaction

[0021]

[0022] It can be seen from the above table that the effect of using 2,6-dimethylpiperazine as the cocatalyst is the best, and the yield is the highest.

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Abstract

A preparation method of α,β-unsaturated ketones, relates to the technical field of preparation of α,β-unsaturated ketone compounds, the present invention uses solid-loaded proline as catalyst and 2,6-dimethylpiperazine as Co-catalyst, under catalysis, aldehyde and acetone are used as reaction raw materials to generate α, β-unsaturated ketone through condensation. The advantages are: (1) The reaction conditions are mild and the synthesis method is simple; (2) The catalyst is stable and can be recycled and reused, and the yield is still higher than 70% after the tenth cycle; (3) The catalyst has a high tolerance to the acidic functional groups of the substrate .

Description

technical field [0001] The invention relates to a synthetic method for preparing ɑ, β-unsaturated ketones. Background technique [0002] α, β -Unsaturated ketones are not only important synthetic building blocks in organic synthesis, but also widely used in many other fields, such as: spices, biopharmaceuticals, pesticides, food and material science, etc. Therefore, this kind of compound has very important research value. Currently, about α, β - There have been many reports in the literature on the research methods of unsaturated ketones, and in these methods, alkaline catalysts and organic solvents are mostly used. The catalysts and solvents used in these methods are harmful to the environment and will cause corrosion to equipment in industrial production , and the solid strong alkaline waste produced after the reaction is also difficult to deal with. These shortcomings limit its large-scale production and application in industry, and at the same time, it does not confor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/00C07C45/72C07C49/217C07C49/235C07C49/255C07C49/248C07C49/21C07C201/12C07C205/45
CPCY02P20/584
Inventor 韩梦婷俞磊
Owner YANGZHOU UNIV