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Synthetic method of benzil derivatives

A synthesis method and technology of derivatives, applied in chemical instruments and methods, preparation of organic compounds, preparation of carbonyl compounds by oxidation, etc., can solve the problem of expensive oxygen source, achieve cheap and easy-to-obtain environment, high yield, and substrate Universal effect

Active Publication Date: 2013-09-18
嘉兴沃特泰科环保科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(3) The oxygen source used is relatively expensive (see Xu, C.-F. et al. Org. Lett., 2011, 13, 1556; Sawama, Y. et al. Eur. J. Org. Chem., 2011, 3361)
[0004] In addition to the above journal literature reports, the Chinese invention patent application document with application number 200910183716.9 discloses an oxidation reaction of internal alkynes catalyzed by an expensive ruthenium-based catalyst, and the reaction needs to be carried out at 80°C; application numbers are 201010018142.2 and 200810021756.9 The Chinese invention patent application literature discloses a milder internal alkyne oxidation reaction, but still uses relatively expensive ruthenium or palladium catalysts

Method used

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  • Synthetic method of benzil derivatives
  • Synthetic method of benzil derivatives
  • Synthetic method of benzil derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023]

[0024] Add 35.6mg (0.2mmol) toluene, 141.7mg (0.4mmol) Selectfluor, 0.64mg (0.01mmol) Cu powder into a 10mL round bottom flask, then add 2mL acetonitrile / water (V:V=50:1) as a solvent. Then, the mixture was magnetically stirred for 4 h at room temperature. Then, 10 g of column chromatography silica gel (100-200 mesh) was added to the reaction solution, and the solvent was removed by distillation under reduced pressure. :1) As an eluent, collect the eluate containing the product, and distill the eluate to remove the solvent to obtain the pure product. The material was a pale yellow oily liquid in 90% yield.

[0025] Characterization data: 1 H NMR (CDCl 3 ,500MHz):δ7.99(dd,J 1 =7.4Hz,J 2 =1.4Hz,4H),7.68(dd,J 1 =7.5Hz,J 2 =1.0Hz,2H),7.53(t,J=7.9,4H); 13 C N MR (CDCl 3 ,125MHz):δ194.6,134.9,133.1,129.9,129.0; m / z(%)=210(20)[M + ],105(100),77(56),51(40).

Embodiment 2

[0027]

[0028] Add 38.4mg (0.2mmol3-methyltoluene), 141.7mg (0.4mmol) Selectfluor, 0.38mg (0.006mmol) Cu powder into a 10mL round bottom flask, then add 2mL acetonitrile / water (V:V=50 : 1) as solvent. Then, the mixture was magnetically stirred for 4 h at room temperature. Then, 10 g of column chromatography silica gel (100-200 mesh) was added to the reaction solution, and the solvent was removed by distillation under reduced pressure. :1) As an eluent, collect the eluate containing the product, and distill the eluate to remove the solvent to obtain the pure product. The material was a pale yellow oily liquid in 78% yield.

[0029] Characterization data: 1 H NMR (CDCl 3,500MHz):δ=7.98(d,J=7.5Hz,2H),7.89(d,J=8.0Hz,2H),7.67(t,J=7.5Hz,1H),7.52(t,J=7.5Hz ,2H),7.32(d,J=8.0Hz,2H),2.45(s,3H);MS(EI,70eV):m / z(%)=224(3)[M + ],119(100).

Embodiment 3

[0031]

[0032] Add 38.4mg (0.2mmol) of 2-methyltoluene, 141.7mg (0.4mmol) of Selectfluor, 0.64mg (0.01mmol) of Cu powder into a 10mL round bottom flask, and then add 2mL of acetonitrile / water (V:V= 50:1) as solvent. Then, magnetic stirring was carried out at room temperature for 8 h. Then, 10 g of column chromatography silica gel (100-200 mesh) was added to the reaction solution, and the solvent was removed by distillation under reduced pressure. :1) As an eluent, collect the eluate containing the product, and distill the eluate to remove the solvent to obtain the pure product. The material was a pale yellow oily liquid, 64% yield.

[0033] Characterization data: 1 H NMR (CDCl 3 ,500MHz):δ=8.0(d,J=7.0Hz,2H),7.68(t,J=7.5Hz,2H),7.55-7.29(m,5H),2.73(s,3H); MS(EI, 70eV):m / z(%)=224(3)[M + ],119(100).

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Abstract

The invention discloses a synthetic method of benzil and derivatives thereof. The diphenylacetylene compound shown in formula I is used as the raw material and is subjected to reaction in a CH3CN / H2O solvent in the presence of a copper catalyst / select flour oxidant system, so as to obtain the benzil derivatives shown in formula II. The synthetic method disclosed by the invention has the advantages of cheap and easily available catalyst, available oxygen source, environment protection, moderate reaction condition, convenient operation and the like, and the functional groups have good universality.

Description

(1) Technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of benzil derivatives. (2) Background technology [0002] Benzil and its derivatives are a special class of organic compounds with extremely wide applications. They can be used as an auxiliary heat stabilizer to overcome the serious shortage of weather resistance of the original metal soap stabilizers, thus greatly expanding the application range of metal soap stabilizers; they can also be combined with a variety of stabilizers The synergistic effect between components and components can effectively improve the thermal stability of plastic products and other properties; its complex with rare earth ions as a catalyst can solve the problem of long-chain branching of traditional catalysts in the synthesis of high molecular weight polyethylene. It can also be used to synthesize imidazoles, benzopyrazines and other drug intermedia...

Claims

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Application Information

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IPC IPC(8): C07C49/784C07C49/813C07C45/28C07C69/76C07C67/313
Inventor 刘运奎张文霞张剑徐振元
Owner 嘉兴沃特泰科环保科技股份有限公司
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