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Preparation method of monobenzo 21-crown-7 and derivative thereof

A kind of derivative and monobenzene technology, applied in the field of preparation of monobenzo-21-crown-7 and its derivatives, can solve the problem of low yield, limited large-scale application, monobenzo-21-crown-7 and its derivatives. Derivative synthesis and processing are cumbersome and other problems, to achieve the effect of good water solubility and easy post-processing

Inactive Publication Date: 2019-06-21
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Thanks to KPF 6 or KBF 4 It can have a strong host-guest interaction with monobenzo 21-crown-7 and its derivatives. The crude product prepared by the template method is the main body formed by monobenzo 21-crown-7 and its derivatives and potassium ions. The guest complex requires repeated washing and multiple column chromatography to remove the template in the product, resulting in very cumbersome synthesis of monobenzo 21-crown-7 and its derivatives, and the yield is not high. At the same time, this processing method Unable to remove all templates in the product
In this way, the large-scale application of monobenzo 21-crown-7 and its derivatives is limited

Method used

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  • Preparation method of monobenzo 21-crown-7 and derivative thereof
  • Preparation method of monobenzo 21-crown-7 and derivative thereof
  • Preparation method of monobenzo 21-crown-7 and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of monobenzo 21-crown-7: 1.1 grams of catechol, 5.91 grams of hexaethylene glycol bis-p-toluenesulfonate, and 5.22 grams of potassium carbonate were reacted at 60°C for 48 hours in 350 milliliters of acetonitrile, and the reaction ended Afterwards, filter while it is hot, remove acetonitrile from the filtrate with a rotary evaporator, dissolve the residue with 250 ml of dichloromethane, wash with water twice, and then remove the dichloromethane with a rotary evaporator to obtain monobenzo 21-crown-7 as 3.23 grams, yield 91%.

[0035] The hydrogen spectrum data are as follows:

[0036] 1 H NMR (400MHz, deuterated chloroform, room temperature): δ6.90(s,4H),4.16(m,4H),3.92(m,4H),3.81(m,4H),3.73(m,4H),3.67 (m,8H).

[0037] Purification: Take 1 gram of the monobenzo21-crown-7 synthesized above, dissolve it in 100 ml of water, stir at room temperature for 12 hours, and then filter it. The obtained filtrate is distilled off under reduced pressure to obtain monoben...

Embodiment 2

[0041] Synthesis of monobenzo 21-crown-7 aldehyde: 1.38 grams of 3,4-dihydroxybenzaldehyde, 5.91 grams of hexaethylene glycol bis-p-toluenesulfonate, and 5.22 grams of potassium carbonate were reacted at 80°C in 350 milliliters of acetonitrile After 48 hours, after the reaction was over, filter while it was hot, remove the acetonitrile from the filtrate with a rotary evaporator, dissolve the residue with 250 ml of dichloromethane, wash with water twice, and then remove the dichloromethane with a rotary evaporator to obtain monobenzo 21- Crown-7 aldehyde is 3.46 grams, and the yield is 90%.

[0042] The hydrogen spectrum data are as follows:

[0043] 1 H NMR (400MHz, deuterated chloroform, room temperature): δ9.87(s, 1H), 7.47(d, J=4Hz, 1H), 7.43(s, 1H), 6.99(d, J=4Hz, 1H), 4.26 (m, 4H), 3.97 (m, 4H), 3.84 (m, 4H), 3.78 (m, 4H), 3.71 (m, 8H).

[0044] Purification: Take 1 gram of the monobenzo 21-crown-7 aldehyde synthesized above, dissolve it in 100 ml of water, stir at roo...

Embodiment 3

[0048] Synthesis of monobenzo 21-crown-7 nitrile: 1.35 grams of 3,4-dihydroxybenzonitrile, 5.91 grams of hexaethylene glycol bis-p-toluenesulfonate, 5.22 grams of potassium carbonate in 350 ml of acetonitrile at 70 ° C React for 48 hours, after the reaction is over, filter while it is hot, use a rotary evaporator to remove acetonitrile from the filtrate, dissolve the residue with 250 ml of dichloromethane, wash with water twice, and then remove the dichloromethane by a rotary evaporator to obtain monobenzo 21 -Crown-7 nitrile is 3.58 grams, and the yield is 94%.

[0049] The hydrogen spectrum data are as follows:

[0050] 1 H NMR (400MHz, deuterated chloroform , room temperature): δ7.27(s,1H)7.10(s,1H)6.99(d,J=4Hz,1H)4.20(m,2H),4.17(m,2H),3.95(m,4H),3.80( m,4H), 3.75(m,4H), 3.68(m,8H).

[0051] Purification: Take 1 gram of the monobenzo 21-crown-7 nitrile prepared by the above synthesis, dissolve it in 100 ml of water, stir at room temperature for 24 hours and then filter,...

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Abstract

The invention discloses a preparation method of monobenzo 21-crown-7 and a derivative thereof. The preparation method comprises the following steps: reacting a catechol compound with hexaethylene glycol di-p-toluenesulfonate for 24-48 hours at the temperature of 60-80 DEG C in presence of an organic solvent and alkali to obtain monobenzo 21-crown-7 and the derivative thereof. According to the preparation method disclosed by the invention, template compounds such as KPF6 or KBF4 are not used in a preparation process, so that the effect of host-guest complexation between a product and potassiumions is avoided, aftertreatment is quite simple and convenient, and the high-purity monobenzo 21-crown-7 and the derivative thereof can be obtained by simple water washing.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of monobenzo 21-crown-7 and derivatives thereof. Background technique [0002] Monobenzo 21-crown-7 and its derivatives are an important class of crown ether compounds, which can coordinate with potassium ions to form stable host-guest complexes. Monobenzo 21-crown-7 and its derivatives are widely used in the preparation of supramolecular polymers, molecular machines, and artificial ion channels. [0003] At present, the synthesis of monobenzo 21-crown-7 and its derivatives mainly adopts the template synthesis method: in the preparation process, KPF 6 or KBF 4 As a template, with acetonitrile as a solvent and potassium carbonate as an acid-binding agent, it is prepared by heating under reflux. Thanks to KPF 6 or KBF 4 It can have a strong host-guest interaction with monobenzo 21-crown-7 and its derivatives. The crude product prepare...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D323/00
Inventor 董盛谊张怡欧阳芸芸
Owner HUNAN UNIV
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