Synthetic method for preparing alpha, beta-unsaturated ketone

A synthesis method and unsaturated technology, applied in the fields of spices, medicines and pesticides, can solve the problems of large waste, great environmental harm, not in line with the spirit of green chemistry, etc., and achieve the effect of eco-friendly and less corrosive equipment

Inactive Publication Date: 2015-07-22
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the catalysts and solvents used in these methods are harmful to the environment and produce a lot of waste, which does not conform to the spirit of green chemistry.

Method used

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  • Synthetic method for preparing alpha, beta-unsaturated ketone
  • Synthetic method for preparing alpha, beta-unsaturated ketone
  • Synthetic method for preparing alpha, beta-unsaturated ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015]

[0016] Mix 2 milliliters of ethanol and 8 milliliters of water to form a 20% ethanol solution by volume.

[0017] In a 50 mL round bottom flask, add 0.074 g calcium hydroxide (1 mmol), dissolve 1.06 g benzaldehyde (10 mmol) and 1.74 g acetone (30 mmol) in the above ethanol solution, and The mixed solution was heated to 50° C. under the protection of nitrogen, and the reaction solution gradually turned light yellow. The reaction was monitored by thin layer chromatography (developing solvent: petroleum ether / ethyl acetate 10:1).

[0018] After 36 h of reaction, the reaction liquid was poured into a mixture of 25 mL ethyl acetate and 30 mL water for extraction, and the aqueous layer was extracted twice with ethyl acetate (20 mL ethyl acetate each time). The organic layers were combined, dried with anhydrous sodium sulfate, filtered, the solvent was evaporated, and the residue was separated by column chromatography to obtain 1.24 g of a light yellow crystal product, n...

Embodiment 2

[0020] Other conditions are the same as in Example 1, and the reaction in different solvents is checked, and the experimental results are shown in Table 1.

[0021] Table 1 Effect of solvent on yield

[0022]

[0023] As can be seen from the above table, 20% ethanol solution is the best solvent (embodiment 1).

Embodiment 3

[0025] Other conditions are the same as in Example 1, and the reaction in different solvents is checked, and the experimental results are shown in Table 2.

[0026] Table 2 Effect of reaction temperature on yield

[0027]

[0028] As can be seen from the table above, 50 degrees has the best effect (Example 1).

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Abstract

The invention provides a synthetic method for preparing alpha, beta-unsaturated ketone, and relates to the technical field of medicines, pesticides, spices and the like. The synthetic method is characterized in that under the catalysis of calcium hydroxide, in a low-concentration alcohol solution, the alpha, beta-unsaturated ketone is directly synthesized by aldehyde ketone through one-step aldol condensation. The calcium hydroxide as a catalyst used in the method is cheap and rich, and after the completion of the reaction, carbon dioxide can be introduced to remove calcium hydroxide. As the method uses the low-concentration alcohol solution, cleanness and environmental protection are achieved. Therefore, the synthetic method is eco-friendly, small in equipment corrosion, durable and more suitable for industrial production.

Description

technical field [0001] The invention relates to the technical fields of medicine, pesticides, spices and the like, in particular to a synthesis method for preparing α,β-unsaturated ketones. Background technique [0002] α,β-unsaturated ketone is an important pharmacophore, which exists in various chemical synthesis and natural active substances such as antineoplastic drugs and plant growth regulators, and is widely used in medicine, pesticides, spices and other fields . There are many methods for the synthesis of α,β-unsaturated ketones, among which α,β-unsaturated ketones are obtained through Aldol condensation reaction of aldehydes and ketones is a relatively common method. That is, aldehydes and ketones are directly synthesized into α, β-unsaturated ketones in organic solvents (usually DMF, methylene chloride, DMSO, etc.) under the action of catalysts (usually solid bases, ionic liquids, fluorine-containing compounds, etc.). However, the catalysts and solvents used in t...

Claims

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Application Information

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IPC IPC(8): C07B37/00C07C45/74C07C49/217C07C49/255C07C49/235C07C49/223C07C201/12C07C205/45C07C49/796C07C49/813C07D213/50C07D333/22
Inventor 俞磊栾洁韩哲刘名轩杨成根
Owner YANGZHOU UNIV
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