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Method for preparing indene compounds

An ester compound and compound technology, applied in the field of preparation of organic compounds, can solve the problems of high cost and time-consuming, and achieve the effects of saving cost, being suitable for mass production, and simplifying the synthesis route.

Active Publication Date: 2008-12-10
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018]In the method provided by the above-mentioned documents, the reaction route is multi-step, very long, too time-consuming, and therefore expensive

Method used

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  • Method for preparing indene compounds
  • Method for preparing indene compounds
  • Method for preparing indene compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of 2,3-dihydro-1-indanone:

[0048] Under the protection of nitrogen, add 85 grams of dipolyphosphoric acid to a one-liter round-bottomed flask equipped with mechanical stirring. After heating to 70 ° C, add 15 grams (0.1 mol) of ethyl benzoate and 2.7 grams of (0.02mol) a homogeneous solution made of anhydrous aluminum trichloride. After stirring for half an hour, the reaction mixture was cooled to below 20°C, and 100 grams of ice water was slowly added to the reaction system, fully stirred and cooled to 50°C-60°C At ℃, add 100 milliliters of n-heptane to extract the mixture, let stand to fully separate the layers, collect the organic layer, wash with saturated sodium bicarbonate solution until alkaline, then dry the organic layer with anhydrous sodium sulfate and remove the solvent to obtain the organic product 10.1 grams, determined by gas chromatography, wherein the 2,3-dihydro-1-indanone content reached 75%. The product was collected after vacuum distill...

Embodiment 2

[0052] The dipolyphosphoric acid in Example 1 was changed to polyphosphoric acid, and the quality and other conditions remained unchanged. After the reaction, 7.5 grams of 2,3-dihydro-1-indanone could be obtained. It can be used in the synthesis of indenoid compounds in the next step.

Embodiment 3

[0054] 85 grams of dipolyphosphoric acid in Example 1 was changed to 45 grams of trifluoromethanesulfonic acid, the reaction temperature was raised to 90°C, and other conditions were unchanged, and 5.8 grams of 2,3-dihydro-1-indanone were obtained after the reaction . It can be used in the synthesis of indenoid compounds in the next step.

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Abstract

The invention discloses a method for preparing an indene compound, comprising the following steps that: a raw material of a substituted benzoic ether compound is converted into an indenone compound under the condition of cyclodehydration in the presence of a Lewis acid compounded organic acid or inorganic acid. The indenone compound is reduced to a hydroxyindane compound by a reducer; the hydroxyindane compound is converted to the indene compound through dehydration. The method of the invention uses the substituted benzoic ether compound which is common and easy to prepare to synthesize the indene compound, thereby simplifying the synthesis route and saving cost and allowing for mass production.

Description

technical field [0001] The invention relates to a preparation method of an organic compound, in particular to a preparation method of an indenoid compound. Background technique [0002] Indene compounds are important intermediates for the synthesis of fine chemicals such as active pharmaceutical components and liquid crystals, and are also important raw materials for the synthesis of polyolefins, especially the active components of metallocene catalysts for polyα-olefins. [0003] Inden compounds can be used to synthesize chiral ansa-metallocene catalyst components with very important three-dimensional structural properties. The catalyst components are coordinated by indene compounds or their derivatives and transition metal compounds that can catalyze olefin polymerization . [0004] Changes in the coordination properties (such as changes in the substituents on the ligand) can lead to changes in the performance of the metallocene catalyst, resulting in changes in the prope...

Claims

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Application Information

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IPC IPC(8): C07C49/67C07C49/755C07C49/697C07C45/61
Inventor 曹育才周慧马静君刘伟
Owner SHANGHAI RES INST OF CHEM IND
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