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Process for the preparation of pillar[5]quinone

a technology of pillar[5]quinone and process, which is applied in the direction of quinone preparation by oxidation and organic chemistry, can solve the problems of environmental hazardous presence of heavy metals in cans, and achieve the effects of good yield, simple and cheap process, and efficient operation

Active Publication Date: 2015-04-30
COUNCIL OF SCI & IND RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This method enables the efficient, simple, and cost-effective production of crystalline pillar[5]quinone with reduced environmental impact, achieving yields of 32% to 34% and providing a stable, crystalline form suitable for various applications such as molecular sensors and electron acceptors.

Problems solved by technology

However, the quinone rings in the aforesaid system do not form part of the cyclamer backbone.
The above process for the synthesis of pillar[5]quinone uses ceric ammonium nitrate (CAN) as an oxidant and the presence of heavy metal in CAN is environmentally hazardous also one of the reactants viz.
2,5-bis(benzyloxymethyl)-1,4-diethoxybenzene is not commercially available and hence it has to be synthesized.

Method used

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  • Process for the preparation of pillar[5]quinone
  • Process for the preparation of pillar[5]quinone
  • Process for the preparation of pillar[5]quinone

Examples

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example 1

[0045]Synthesis of Pillar [5] quinone

[0046]A single-necked 2L round bottom flask was charged with finely ground 1,4-dimethoxypillar[5]arene (25.0 g, 33.3 mmol), acetonitrile (350 mL) and a solution of ozone (2KHSO5.KHSO4K2SO4, 122.9 g, 400.0 mmol) in water (350 mL). To the above mixture, iodobenzene (7.5 mL, 66.6 mmol) was added. The reaction mixture, after vigorously stirring at room temperature (25° C.) for 48 hours, was poured into water and filtered under suction. The yellow colored residue was repeatedly washed with plenty of water followed by methanol and dried.

Purification Carried Out by the Following Crystallization Procedure

[0047]The crude compound (18.264 g) was first dissolved in boiling 1,1,2,2-tetrachloroethane (TCE, 350 mL), and filtered under suction to remove some undissolved brownish material (0.813 g), which was discarded. The reddish-colored clear filtrate was left at room temperature (25° C.) for 6 hrs (substantial amount of P[5]Q crystallized out during this per...

example 2

[0050]Surface Characterization of Pillar[5]quinone

[0051]In order to determine the morphology and topography of the Pillar[5]quinone, crystallized from the 1,1,2,2-tetrachloroethane SEM, TEM and AFM were obtained.

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Abstract

The present invention relates to a process for the preparation of pillar[5]quinone and further relates to an easy-to-operate and chromatography-free process for the preparation of crystalline pillar [5] quinone by the oxone / iodobenzene-mediated oxidative de-aromatization of readily available 1,4-dimethoxypillar[5] arenes in good

Description

FIELD OF THE INVENTION[0001]The present invention relates to a process for the preparation of pillar[5]quinone. More particularly, the present invention relates to crystalline form of pillar[5]quinone and an easy-to-operate, chromatography-free process for the preparation of crystalline pillar[5]quinone from 1,4-dimethoxypillar[5]arenes.BACKGROUND OF THE INVENTION[0002]Pillar[5]arenes, a new class of fascinating cyclophanes, continue to attract the attention of chemists and the interest in this class of macrocycles continues unabated primarily due to their enormous application potential in diverse areas. The most notable feature of pillar[5]arenes is their deep π-encircled internal cavity capable of accommodating guest molecules through diverse non-covalent interactions, thereby raising the hope of developing molecular sensors. It is noteworthy that by virtue of their structural architecture, cycloquinones decorated with deep internal cavity essential for molecular sensing, are also...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C46/02
CPCC07C46/02C07C2603/90C07C50/22
Inventor GANGADHAR, JESSY SANJAYANKILINGARU, ISHWARA SHIVAKUMAR
Owner COUNCIL OF SCI & IND RES