Preparation method of 4,4'-dinitrobibenzils compound

A dinitrobibenzyl compound technology, applied in 4 fields, can solve problems such as difficult separation, difficult storage, complicated operation, etc., and achieve the effects of reducing environmental pollution, reducing experimental costs, and easy separation and purification

Inactive Publication Date: 2009-02-11
SHANXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These preparation methods mainly focus on the selection of strong base and solvent, such as those reported in the literature: potassium tert-butoxide / tert-butanol, potassium tert-butoxide / DMSO, KNH 2 / THF, Na / CH 3 OH, CH 3 ONa / CH 3 OH, KOH / CH 3 OH, etc. Most of these methods use unstable, difficult to preserve, high-cost strong bases and flammable and volatile organic solvents, and it is easy to generate further oxidative coupling by-products 4,4'-dinitrostilbene , so that the cost of the experiment is high, the operation is complicated, the separation is difficult, and the environmental pollution is serious

Method used

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  • Preparation method of 4,4'-dinitrobibenzils compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1 4, the preparation of 4'-dinitrobibenzyl

[0021] (1) Add 1.42g (1.25mmol) β-cyclodextrin, 2.2g sodium hydroxide and 10ml water successively in the reaction vessel equipped with electromagnetic stirrer, reflux condenser and thermometer, stir at room temperature until clarified, then Add 0.17g (1.25mmol) p-nitrotoluene, raise the temperature to about 55°C and react for 12h;

[0022] (2) Stop the reaction, place to precipitate, and filter with suction to obtain 0.15 g of yellow solid crude product;

[0023] (3) fully wash this solid 3 times with boiling hexanaphthene, to remove unreacted raw material;

[0024] (4) Extract the solid obtained in step (3) with boiling benzene for 3 times, discard the insoluble impurities, spin the gained benzene solution to obtain the product 4,4'-dinitrobibenzyl 0.1g, and the yield is 59 %. m.p.180~181℃, 1 HNMR (300MHz, CDCl 3 )δ: 8.142-8.114 (4H, d), 7.277-7.243 (4H, d), 3.058 (4H, s).

Embodiment 2

[0025] Example 2 Preparation of 2,2'-difluoro-4,4'-dinitrobibenzyl

[0026] (1) Add 1.42g (1.25mmol) β-cyclodextrin, 2.2g sodium hydroxide and 10ml water successively in the reaction vessel equipped with electromagnetic stirrer, reflux condenser and thermometer, stir at room temperature until clarified, then Add 0.2g (1.25mmol) 2-fluoro-4-nitrotoluene, raise the temperature to about 55°C and react for 4h;

[0027] (2) Stop the reaction, place to precipitate out, and filter with suction to obtain 0.21 g of yellow solid crude product;

[0028] (3) fully wash this solid 3 times with boiling hexanaphthene, to remove unreacted raw material;

[0029] (4) Extract the solid obtained in step (3) with boiling benzene for 3 times, discard the insoluble impurities, and spin the obtained benzene solution to obtain the product 2,2'-difluoro-4,4'-dinitrobi 0.14 g of benzyl, the yield is 70%. m.p.145~147℃, 1 HNMR (300MHz, CDCl 3 )δ: 7.942-7.878 (4H, t), 7.281-7.255 (2H, d), 3.059 (4H, s)...

Embodiment 3

[0030] Example 3 Preparation of 2,2'-dichloro-4,4'-dinitrobibenzyl

[0031] (1) Add 1.42g (1.25mmol) β-cyclodextrin, 2.2g sodium hydroxide and 10ml water successively in the reaction vessel equipped with electromagnetic stirrer, reflux condenser and thermometer, stir at room temperature until clarified, then Add 0.22g (1.25mmol) 2-chloro-4-nitrotoluene, raise the temperature to about 55°C and react for 6h;

[0032] (2) Stop the reaction, place to precipitate out, and filter with suction to obtain 0.2 g of yellow solid crude product;

[0033] (3) fully wash this solid 3 times with boiling hexanaphthene, to remove unreacted raw material;

[0034] (4) Extract the solid obtained in step (3) with boiling benzene for 3 times, discard the insoluble impurities, and spin the obtained benzene solution to obtain the product 2,2'-dichloro-4,4'-dinitrobi Benzyl 0.14g, the yield is 64%. m.p.161~163℃, 1 HNMR (300MHz, CDCl 3 )δ: 8.244 (2H, s), 8.028 ~ 8.001 (2H, d), 7.291 ~ 7.263 (2H, d)...

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Abstract

The invention provides a preparation method of 4,4'-dinitro bibenzyl compound. The method is as follows: paranitrotoluene compounds, beta-cyclodextrin and sodium hydroxide are dissolved in water and react under the certain temperature. Then the prepared solid crude product is washed with cyclohexane and extracted with benzene to obtain the product of the invention. The preparation method of the invention has the advantages of low cost, simple operation, easy separation and purification and little environmental pollution.

Description

technical field [0001] The invention relates to 4,4'-dinitrobibenzyl compounds, in particular to a preparation method of 4,4'-dinitrobibenzyl compounds. Background technique [0002] 4,4'-Dinitrobibenzyl compounds are important fine organic chemical raw materials and synthetic intermediates, mainly used in the fields of medicine, cosmetics, dyes and engineering resins, so their synthesis has always attracted the attention of chemists. The industrial preparation of 4,4'-dinitrobibenzyl compounds is obtained by the interaction of p-nitrotoluene compounds with strong bases to lose a-H, and then oxidative coupling in oxygen or air atmosphere. These preparation methods mainly focus on the selection of strong base and solvent, such as those reported in the literature: potassium tert-butoxide / tert-butanol, potassium tert-butoxide / DMSO, KNH 2 / THF, Na / CH 3 OH, CH 3 ONa / CH 3 OH, KOH / CH 3 OH, etc. Most of these methods use unstable, difficult to preserve, high-cost strong bases a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/06C07C205/11
Inventor 刘宇芳刘博董振明金硕
Owner SHANXI UNIV
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