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Method for preparing 2-alkylene cyclobutanone

A technology of hydrocarbylene cyclobutanone and hydrocarbyl cyclobutanone, which is applied in the field of synthesis of new synthetic building block methylene cyclobutanone, can solve the problems of long route, limited application, harsh conditions required for reaction, etc., and achieve high efficiency , short route and low catalyst cost

Inactive Publication Date: 2012-06-20
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, at present, the method for synthesizing 2-alkylene cyclobutanone is relatively long, and the conditions required for some reactions are harsh (need to use metal sodium sand, in anhydrous anhydrous Oxygen), and use expensive gold catalysts (Markham, J. P.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc.2005, 127, 9708-9709. Since cyclopropanone cannot exist stably, there is no ready-made product available, and it needs to be prepared indirectly through multi-step reactions of ethyl chloropropionate, as shown in the following formula)
These disadvantages limit the application of this method

Method used

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  • Method for preparing 2-alkylene cyclobutanone
  • Method for preparing 2-alkylene cyclobutanone
  • Method for preparing 2-alkylene cyclobutanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] 1. Reaction formula:

[0020]

[0021] 2. The amount and properties of the reaction raw materials:

[0022] substance molecular weight millimoles Mass / g Volume / mL Cyclobutanone 70 30 2.1 Benzaldehyde 106 10 1.06 sodium hydroxide 40 0.2 0.008 ethanol 10

[0023] 3. Operation process:

[0024] In a 50 mL round bottom flask, add cyclobutanone, benzaldehyde, ethanol, and sodium hydroxide in sequence, and stir at room temperature at 20°C (the dosage is shown in the table above). The reaction solution gradually turned light yellow. The reaction was monitored by thin layer chromatography (developing solvent: petroleum ether: ethyl acetate 5:1).

[0025] After the reaction was completed for 1 h, 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 la...

Embodiment 2

[0028] 1. Reaction formula:

[0029]

[0030] two,

[0031] Numbering R 1 R 2 Yield(%) 1 p -MeC 6 h 4 H 74 2 p -MeOC 6 h 4 H 80 3 p -ClC 6 h 4 H 56 4 C 7 h 15 H 33 5 C 6 h 5 CH 3 53 6 C 6 h 5 C 6 h 5 58 7 C 3 h 7 CH 3 23

[0032] Replace benzaldehyde with other aldehydes and ketones, and other conditions are the same as in Example 1, and the experimental results are as shown in the table above.

[0033] The above table shows that this method has a wide range of applications, and both aldehydes and ketones can be used to synthesize corresponding compounds.

Embodiment 3

[0035] solvent water Methanol Isopropanol Product yield (%) 47 60 64

[0036] Replace ethanol with other solvents, and other conditions are the same as Example 1, and the experimental results are shown in the table above.

[0037] The above table shows that under the same other conditions, the yield of ethanol is the highest.

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Abstract

Provided is a method for preparing 2-alkylene cyclobutanone. The method relates to the technical field of synthesis methods of synthesized building block alkylene cyclobutanone and includes that cyclobutanone and aldehyde ketone serve as raw materials, are catalyzed by alkali and performed with aldol condensation, and directly synthesize the complex 2-alkylene cyclobutanone in one step. Compared with the traditional synthesis methods, the method for preparing 2-alkylene cyclobutanone is simple, short in line and mild in reaction conditions, the raw materials are easy to obtain, and reaction is easy to operate. By using the method for preparing 2-alkylene cyclobutanone, synthesizing cost is greatly reduced, synthesizing work load is reduced, and efficiency is improved.

Description

technical field [0001] The present invention relates to a kind of synthetic method of novel synthetic block methylene cyclobutanone. Background technique [0002] Organic molecules containing both small-sized carbon rings (three-membered rings or four-membered rings) and extracyclic double bonds have higher intramolecular tension, and can undergo many unique organic chemical reactions under milder conditions. Therefore, they are important organic synthesis building blocks in organic synthesis. In recent years, there have been many studies on alkylene cyclopropanes, and a large number of literatures have reported their application in organic synthesis. Alkylenecyclobutanes are sister molecules of alkylenecyclopropanes and, therefore, may also serve as useful building blocks in organic synthesis. However, from the current literature reports, most of the four-membered rings have not been touched in the reaction of alkylene cyclobutane due to the less tension of the four-membe...

Claims

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Application Information

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IPC IPC(8): C07C45/74C07C49/683C07C49/753C07C49/697C07C49/647
Inventor 俞磊吴于兰陈天易容
Owner YANGZHOU UNIV
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