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Method for synthesizing nitrile from aldoxime

An aldoxime and compound technology, applied in the field of synthesizing nitrile, can solve the problems of large amount, unsuitable for mass production, expensive palladium catalyst and the like, and achieves the effects of high yield, easy availability of raw materials and strong atom economy

Inactive Publication Date: 2012-03-07
YANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reported catalytic dehydration methods still have some limitations, either using expensive palladium catalysts and using large amounts (Kim, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett.2009 . 50, 1717.), or need to react in ultrasound, not suitable for mass production (Jiang, N.; Ragauskas, A. J. Tetrahedron Lett.2010, 51, 4479.)

Method used

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  • Method for synthesizing nitrile from aldoxime
  • Method for synthesizing nitrile from aldoxime

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] 1. Reaction formula:

[0017]

[0018] 2. Raw materials and properties of each raw material:

[0019] substance molecular weight millimoles Mass / g Volume / mL Benzaldehyde oxime 121 200 24.2 copper trifluoroacetate 289.6 2 0.58 manganese dioxide 87 6 0.52 Triphenylphosphine 262 8 2.10 Acetonitrile 400

[0020] 3. Operation process:

[0021] Add benzaldoxime, copper trifluoroacetate, manganese dioxide, triphenylphosphine, and acetonitrile in sequence in a 1 L round bottom flask, connect the reflux condenser, and stir under reflux (81°C) (the amount of feed is shown in the table above ). The reaction solution gradually turned yellow. The reaction was monitored by thin-layer chromatography (developing solvent: petroleum ether / ethyl acetate 6:1). The reaction was completed after 12 h, and the distillation device was connected for distillation, and the solvent acetonitrile (79-81 ℃...

Embodiment 2

[0023] 1. Reaction formula:

[0024]

[0025] Other aldoximes are used to replace benzyl aldoxime, and other conditions are the same as in Example 1, and the experimental results are shown in the following table.

[0026]

[0027] Numbering R Yield(%) 1 p -MeC 6 h 4 95 2 p -MeOC 6 h 4 91 3 p-HOC 6 h 4 88 4 p -Bu t C 6 h 4 71 5 4-Me 2 NC 6 h 4 74 6 p -ClC 6 h 4 72 7 p -BrC 6 h 4 84 8 m-BrC 6 h 4 61 9 m-NO 2 C 6 h 4 70 10 E -C 6 h 5 CH=CH 70 11 C 7 h 15 96

[0028] It can be seen from the above table that this reaction has a wide range of applications, and no matter aromatic aldoxime, alkyl aldoxime or cinnamyl aldoxime can be easily converted into nitriles.

Embodiment 3

[0030] solvent Adiponitrile Dimethyl sulfoxide N, N-Dimethylformamide Product yield (%) 61 47 52

[0031] Replace acetonitrile with other solvents, other conditions are the same as Example 1, and the experimental results are shown in the table above.

[0032] As can be seen from the above table, the reaction can be carried out in polar solvents, among which the best effect is in acetonitrile.

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Abstract

The invention discloses a green and practical method for synthesizing nitrile from aldoxime. According to the invention, oxime is adopted as a raw material. Under the catalysis of a copper-manganese-phosphor composite catalyst, oxime is dehydrated into nitrile. Compared to a traditional synthesizing method, a dehydration agent with equivalent weight is not required, and no harmful waste is produced. The method is simple and is easy to operate. The raw materials are easy to obtain. The method is suitable to be used in medicine synthesizing and productions of fine chemical intermediates.

Description

technical field [0001] The present invention relates to a kind of synthetic method of synthesizing nitrile. Background technique [0002] Nitrile is a class of useful compounds and an important raw material in chemical production. Nitrile is widely used in medicinal chemistry and pesticide chemistry. Since aldehydes are easy to obtain and can be easily converted into aldoximes, it is feasible to develop a strategy to synthesize nitriles from aldoximes. At present, many methods for the synthesis of nitriles from aldoximes have been developed. However, in these methods, it is often necessary to use toxic or corrosive dehydrating agents and generate a large amount of waste. The development of a dehydrating agent-free catalytic dehydration reaction to prepare nitriles from aldoximes is an efficient and environmentally friendly organic synthesis strategy. Recently, this strategy has been reported in the literature. However, the reported catalytic dehydration methods still ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/00C07C255/50C07C255/54C07C255/53C07C255/58C07C255/34C07C255/03B01J31/32
Inventor 俞磊易容陈天吴于兰徐清
Owner YANGZHOU UNIV
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