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Synthetic method of diaryl macrocyclic crown ether compound

A synthesis method and compound technology, applied in the direction of organic chemistry, etc., can solve the problems of low yield, unsatisfactory atomic economics and green chemistry, unfavorable use, etc., and achieve high total yield, short synthesis route, and simple operation. Effect

Inactive Publication Date: 2014-09-17
SOUTH CHINA NORMAL UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such a low yield is not conducive to its use in molecular machine research, and it is also unsatisfactory from the perspective of atomic economics and green chemistry

Method used

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  • Synthetic method of diaryl macrocyclic crown ether compound
  • Synthetic method of diaryl macrocyclic crown ether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] (1) Synthesis of triethylene glycol disulfonate

[0020] Weigh p-toluenesulfonyl chloride (62.34g, 0.327mol) and triethylene glycol (16.37g, 0.11mol) and grind them in a mortar for 30 minutes, then add sodium hydroxide (17.44g, 0.436mol) and continue grinding until a large amount of white appears The solid was recrystallized from ethanol to obtain 46.5 g of white crystals, with a yield of 93%.

[0021] (2) One-step synthesis of dibenzo-24-crown-8

[0022] After dissolving 0.5506g (1mmoml) catechol and 2.294g (5mmol) triethylene glycol disulfonate with 15ml dimethylformamide, they were added to a constant pressure dropping funnel, and 0.1519g (1mmol) was dissolved under nitrogen protection. Cesium fluoride, 1.303g (4mmol) cesium carbonate, 20mg tetrabutylammonium iodide (in other examples, the catalyst may be tetrabutylammonium bromide) are quickly added to a 250ml round bottom containing 70ml dimethylformamide In the flask, the samples in the dropping funnel were adde...

Embodiment 2

[0024] (1) Synthesis of triethylene glycol disulfonate

[0025] Weigh p-toluenesulfonyl chloride (62.34g, 0.327mol) and triethylene glycol (16.37g, 0.11mol) and grind in a mortar for 30min, add sodium hydroxide (17.44g, 0.436mol) and grind until a large amount of white solid appears. Recrystallization with ethanol gave 46.5 g of white crystals with a yield of 93%.

[0026] (2), one-step synthesis of dibenzo-26-crown-8

[0027] After dissolving 0.5506g (1mmoml) resorcinol and 2.294g (5mmol) triethylene glycol disulfonate with 15ml dimethylformamide, they were added to a constant pressure dropping funnel, and 0.1519g (1mmol) was dissolved under nitrogen protection. Cesium fluoride, 1.303g (4mmol) cesium carbonate, 20mg tetrabutylammonium iodide were quickly added to a 250ml round bottom flask containing 80ml dimethylformamide, and the samples in the dropping funnel were added dropwise in batches, under nitrogen protection Reflux reaction for 5 days, the reaction temperature is...

Embodiment 3

[0029] (1) Synthesis of triethylene glycol disulfonate

[0030] Weigh p-toluenesulfonyl chloride (62.34g, 0.327mol) and triethylene glycol (16.37g, 0.11mol) and grind in a mortar for 30min, add sodium hydroxide (17.44g, 0.436mol) and grind until a large amount of white solid appears. Recrystallization with ethanol gave 46.5 g of white crystals, yield: 93%.

[0031] (2), one-step synthesis of dibenzo-28-crown-8

[0032] After dissolving 0.5506g (1mmoml) hydroquinone and 2.294g (5mmol) triethylene glycol disulfonate with 15ml dimethylformamide, they were added to a constant pressure dropping funnel, and 0.1519g (1mmol) was dissolved under nitrogen protection. Cesium fluoride, 1.303g (4mmol) cesium carbonate, 20mg tetrabutylammonium iodide were quickly added to a 250ml round-bottomed flask filled with 75ml dimethylformamide, and the samples in the dropping funnel were added dropwise in batches under nitrogen protection. Reflux reaction for 5 days, the reaction temperature is 10...

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Abstract

The invention discloses a synthetic method of a diaryl macrocyclic crown ether compound; firstly, p-toluene sulfonyl chloride is reacted with polyglycol to obtain polyglycol disulfonate, and then the polyglycol disulfonate is reacted with a diphenolic compound in the presence of an organic solvent, an alkali metal salt and a catalyst; the polyglycol is either triethylene glycol or tetraglycol, and the catalyst is one of tetrabutylammonium iodide or tetrabutylammonium bromide. According to the method, the tetrabutylammonium iodide or the tetrabutylammonium bromide is used as the catalyst for catalysis of the reaction of the diphenolic compound and the polyglycol disulfonate for preparation of the diaryl macrocyclic crown ether compound, the total yield is 18-50%, the total yield is high, the synthetic route is short, the operation is simple, and the method is a synthetic method worthy of popularization.

Description

technical field [0001] The invention relates to the technical field of crown ether synthesis, in particular to a synthesis method of a diaryl macrocyclic crown ether compound. Background technique [0002] Macrocyclic crown ethers have the ability to selectively complex metal ions, and have obvious choices for the complexation of different metal ions with the change of the type of heteroatoms in the macrocyclic ligand, the number of atoms and the size of the macrocyclic hole. sex. Therefore, macrocyclic crown ethers immediately attracted the attention of chemists from all over the world, and a wave of research was quickly set off. The research on crown ether chemistry and its applications was carried out rapidly, and penetrated into many branches of chemistry, such as organic synthesis and polymer synthesis. , coordination chemistry, analytical chemistry, extraction chemistry, metal and isotope separation, identification and resolution of optical isomers, and penetration in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D323/00
CPCC07D323/00
Inventor 蒋腊生肖瑞陈玉磊陈木娟黄伟聪黎汉超欧博明
Owner SOUTH CHINA NORMAL UNIVERSITY