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Process for preparing 1,1'-spiro indan or derivatives thereof

A technology of spirodihydroindane and its derivatives, which is applied in the field of organic compound preparation chemistry, can solve problems such as product separation troubles, equipment corrosion, etc., and achieve the effects of low cost, less pollution, and easy availability of raw materials

Inactive Publication Date: 2006-09-06
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In short, product separation is very troublesome
In addition, since polyphosphoric acid and phosphorus oxychloride are liquid acids, the corrosion of equipment is also serious.

Method used

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  • Process for preparing 1,1'-spiro indan or derivatives thereof
  • Process for preparing 1,1'-spiro indan or derivatives thereof
  • Process for preparing 1,1'-spiro indan or derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] 4.8 g (20 mmol) of 1,5-diphenyl-3-pentanone, 3 g (1 mmol) of silicomolybdic acid and 60 ml of benzene were added to a flask. Install the water separator, reflux the condenser, heat and reflux for dehydration. After the reaction, the insoluble solid was removed by filtration and washed with chloroform, the organic phases were combined, and the solvent was evaporated. A light yellow liquid was obtained, which was purified by silica gel column chromatography to obtain 2.6 g of 1,1'-spirodihydroindene as a colorless liquid, with a yield of 60%. Proton NMR spectrum (300M, deuterium): 2.14-2.35 (m, 4H) 3.02 (t, J = 13Hz, 4H) 6.92 (d, J = 7Hz, 2H) 7.11-7.29 (m, 6H); infrared: 1602, 1455, 751 (cm -1 ).

[0016]

[0017] 1,5-Diphenyl-3-pentanone 1,1'-spirodihydroindane

Embodiment 2

[0019] 4.8 g (20 mmol) of 1,5-diphenyl-3-pentanone, 14 g (5 mmol) of phosphomolybdic acid and 60 ml of toluene were added to a flask. Install the water separator, reflux the condenser, heat and reflux for dehydration. After the reaction, the insoluble solid was removed by filtration and washed with chloroform, the chloroform and toluene were combined, and the solvent was removed by rotary evaporation. A pale yellow liquid was obtained, which was purified by silica gel column chromatography. 1,1'-spirodihydroindane was obtained as 4 g of colorless liquid with a yield of 91%. Proton NMR spectrum (300M, deuterium): 2.14-2.35 (m, 4H) 3.02 (t, J = 13Hz, 4H) 6.92 (d, J = 7Hz, 2H) 7.11-7.29 (m, 6H); infrared: 1602, 1455, 751 (cm -1 ).

Embodiment 3

[0021] Add 5.3 g (20 mmol) of 2,5-dibenzylcyclopentanone, 14.4 g (5 mmol) of silicotungstic acid and 60 ml of toluene into a flask. Install the water separator, reflux the condenser, heat and reflux for dehydration. After the reaction, the insoluble solid was removed by filtration and washed with chloroform, the chloroform and toluene were combined, and the solvent was removed by rotary evaporation. A light yellow solid was obtained, which was recrystallized from methanol. 2,2'-Ethylene-1,1'-spirodihydroindene was obtained as 3.8 g of a colorless solid with a melting point of 100-102°C and a yield of 77%.

[0022]

[0023] 2,5-Dibenzylcyclopentanone 2,2'-Ethylene-1,1'-spirodihydroindane

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Abstract

The invention relates to a method for preparation of 1,1íõ-spirobiindane or its derivant with the method of dehydration of 1, 5-diaryl-3-pentanone catalyzed and cyclized by heteropoly acid.The said 1,1íõ-spirobiindane or its derivant is obtained by refluxing and dewatering the 5-diaryl-3-pentanone and heteropoly acid in the flow of aromatic hydrocarbon until it is of no water, filtering the heteropoly acid and purifying the mother liquid with a yield rate of 57-91 %. The method is characterized in that it is of easy technology, low cost and slight pollution.

Description

technical field [0001] The invention describes a method for preparing 1,1'-spirodihydroindane or its derivatives from 1,5-diaryl-3-pentanone through heteropolyacid catalyzed cyclodehydration, and belongs to the field of organic compound preparation chemistry. Background technique [0002] 1,1′-spirodihydroindane derivative is a kind of typical C 2 Compounds with axes of symmetry. They have unique structural and physicochemical properties and have received increasing attention in recent years. As chiral ligands, 1,1'-spiroindane-7,7'-diol and its derivatives have shown good activity in various asymmetric catalysis. On the other hand, 1,1'-spiroindene derivatives are also precursors of optical materials with good properties. [0003] The preparation methods of 1,1'-spirodihydroindene can be divided into two categories. The first category is to prepare 1,1'-spirobiindene or 1,1'-spirobiindene and then reduce them to obtain 1,1 '-spirodihydroindane. The second type is to pr...

Claims

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Application Information

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IPC IPC(8): C07C1/24C07C13/62
Inventor 单自兴兰鲲
Owner WUHAN UNIV
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