Chemical synthesis method of O-acylcalix[4]arene

A technology of chemical synthesis and synthesis method, which is applied in the field of preparation of O-acylcalix[4]arene, which can solve the problems of difficult recovery, large amount of catalyst, and large amount of solvent, etc., and achieves mild reaction conditions, high reaction yield, and environmental friendliness Effect

Active Publication Date: 2010-07-21
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the disadvantages of O-acylcalix[4]arenes in the prior art that the preparation of O-acyl calix[4]arene requires a large amount of catalyst, a large amount of solvent, and is difficult to recycle, the present invention provides a method with reasonable process, high reaction yield, low catalyst amount and can be used. Green chemical synthesis of O-acylcalix[4]arenes with convenient recycling, low production cost and environmental protection

Method used

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  • Chemical synthesis method of O-acylcalix[4]arene
  • Chemical synthesis method of O-acylcalix[4]arene

Examples

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Embodiment 1

[0020] In a two-necked flask, put 1.0 g (1.54 mmol) of tetra-tert-butylcalix[4]arene, add 20 mL of chloroform and stir to dissolve, add 0.0154 mmol of zinc trifluoromethanesulfonate, and add 1.2 g (0.012 mol) of acetic anhydride , reacted at 50°C for 2 hours, added 15ml of water and stirred for 30min after the reaction was completed, the water layer was separated, and the organic layer was evaporated to remove the solvent to obtain a yellow crude product, which was reconstituted with 20ml of dichloromethane / methanol (mixed by volume ratio 1:1) Crystallized to obtain 1.1 g of pure white product with a yield of 87% and a melting point of 320°C.

Embodiment 2

[0022] In a two-necked flask, put 1.0 g (1.54 mmol) of tetra-tert-butylcalix[4]arene, add 25 mL of chloroform and stir to dissolve, add 0.0231 mmol of bismuth trifluoromethanesulfonate, and add 1.2 g (0.012 mol) of acetic anhydride , reacted at 20°C for 2 hours, added 15ml of water and stirred for 30min after the reaction was completed, the water layer was separated, and the organic layer was evaporated to remove the solvent to obtain a yellow crude product, which was reconstituted with 20ml of dichloromethane / methanol (mixed by volume ratio 1:1) Crystallized to obtain 0.9 g of pure white product with a yield of 72% and a melting point of 320°C.

Embodiment 3

[0024] In a two-necked flask, put 1.0 g (1.54 mmol) of tetra-tert-butylcalix[4]arene, add 25 mL of chloroform and stir to dissolve, add 0.0308 mmol of ytterbium trifluoromethanesulfonate, and add 1.2 g (0.012 mol) of acetic anhydride , reacted at 20°C for 10 hours, after the reaction was completed, add 10ml of water and stir for 30min, the water layer was separated, and the organic layer was evaporated to remove the solvent to obtain a yellow crude product, which was reconstituted with 20ml of dichloromethane / methanol (mixed by volume ratio 1:1) Crystallized to obtain 0.85 g of white pure product, the yield was 67%, and the melting point was 320°C.

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Abstract

The invention relates to a chemical synthesis method of O-acylcalix[4]arene shown in the formula (I). The synthesis method comprises the following steps: dissolving the calixarene shown in the formula (II) in organic solvent, reacting with the acylation reagent shown in the formula (IV) at 0-150 DEG C for 0.1-10 hours under the catalysis of lithiumtrifluoromethanesulfonate shown in the formula (III), and reprocessing reaction liquid to obtain O-acylcalix[4]arene shown in the formula (I), wherein in the formula (I) and (II), R1 represents C1-C6 alkyl or hydrogen; in the formula (I) and (IV), R2 represents C1-C6 alkyl, phenyl or benzyl; and in the formula (IV), X is Cl or R2COO. The beneficial effects of the invention are as follows: the catalyst used in the reaction can be reused; the yield is high (generally over 80%); the process route is advanced, the reaction conditions are mild; and the amount of catalyst is small and the method is environmentally friendly.

Description

(1) Technical field [0001] The invention relates to a green synthesis method of O-acyl calix [4] arenes, in particular to using Lewis acid catalyst triflate to prepare O-acyl calix [4] arenes. (2) Background technology [0002] At present, the synthesis of O-acylcalix[4]arenes uses traditional acids or bases such as concentrated sulfuric acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid, aluminum chloride, and pyridine as catalysts. For example, Tetrahedron 1982, 38, 373 proposed to use catalytic amount of p-toluenesulfonic acid as a catalyst, acetic anhydride as a solvent, and refluxed for 20 hours to obtain the target product with a yield of 54%. Tetrahedron 1987, 43, 4917 proposed to use 7 equivalents of strong base NaH As a catalyst to complete the benzoylation of phenolic hydroxyl group, the yield is 80%. [0003] Traditional protonic acid and organic base can catalyze the reaction at high temperature to obtain the corresponding O-acylated product with a yiel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/14C07C67/08C07C69/017C07C69/21C07C69/78
CPCY02P20/582Y02P20/584
Inventor 金灿苏为科王悠然
Owner ZHEJIANG UNIV OF TECH
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