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Method for preparing indanone compounds

A compound and acidic compound technology, applied in the field of preparation of organic compounds, can solve problems such as time-consuming and expensive, and achieve the effects of saving costs, being suitable for mass production, and simplifying synthetic routes

Active Publication Date: 2009-01-07
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 indanone compounds
  • Method for preparing indanone compounds
  • Method for preparing indanone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Synthesis of 2-methyl-2,3-dihydro-1-indanone:

[0043] a) Add 400mL of ethanol to a 2000mL four-necked reaction flask equipped with stirring, heating, reflux condenser, thermometer, dropping funnel and drying tube, then add 1 mole of sodium ethylate, and stir to dissolve. After the temperature of the reaction system drops to 30°C, add 1 mole of diethyl methylmalonate dropwise to the reaction flask, then add 1 mole of benzyl chloride to the reaction mixture, and stir the reaction between 40-60°C. GC monitors until the raw materials disappear, it takes about 2 hours, then add 800mL water to the reaction bottle to dilute the reaction mixture, then add 500mL n-hexane, stir well, separate layers, collect the organic layer, and then distill off the solvent n-hexane and a small amount of ethanol 245 g of diethyl 2-benzyl-2-methylmalonate was obtained with a yield of 92.7%. The purity of the product was about 95% by GC analysis. It was used in the next step without purification...

Embodiment 2

[0048] Synthesis of 2,3-dihydro-1-indanone:

[0049] Replace the diethyl methylmalonate in Example 1 with diethyl malonate in an equimolar amount, and keep other operating conditions unchanged to obtain 221 grams of diethyl 2-benzyl malonate, with a yield of 88.3% , 97% purity. Get 0.5mol of gained 2-benzyl malonate diethyl ester, according to the b) step condition reaction of embodiment 1, obtain 2,3-dihydro-1-indanone 51.7 grams with 78.2% yield, product purity 98.6%.

[0050] The spectrogram data is as follows:

[0051] 1 H NMR (300MHz, CDCl 3 ): δ=2.4-2.6(t, 2H), δ=3.02-3.09(t, 2H), δ=7.15-7.25(t, 2H), δ=7.60-7.69(t, 1H), δ=7.87- 7.96(d, 1H).

Embodiment 3

[0053] Synthesis of 4-chloro-2-ethyl-2,3-dihydro-1-indanone:

[0054] a) Add 400mL of N,N-dimethylformamide (DMF) to a 2000mL four-necked reaction flask with stirring, heating, reflux condenser, thermometer, dropping funnel and drying tube, and then add 1 mole of tert-butyl Sodium alkoxide, stir well to dissolve. When the temperature of the reaction system drops to 30°C, add 1 mole of diethyl ethylmalonate dropwise to the reaction flask, then add 1 mole of o-chlorobenzyl chloride to the reaction mixture, and stir the reaction at 40-60°C , GC monitors until the raw materials disappear, it takes about 1 hour, then add 800mL water to the reaction bottle to dilute the reaction mixture, then add 500mL n-heptane, stir well and separate the layers, collect the organic layer, then distill off the solvent n-heptane and After a small amount of water, 292.8 grams of 2-(2-chlorobenzyl)-2-ethylmalonate diethyl ester was obtained, with a yield of 93.6%. The product was analyzed by GC with ...

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Abstract

The invention provides a method for preparing an indanone compound, which comprises the following steps: selecting a substituted benzyl halide compound as a raw material, carrying out coupling reaction with malonate to generate a substituted malonate compound; and directly synthesizing a substituted indanone compound from the substituted malonate compound in the presence of a phosphoric acid-containing compound. The method can synthesize the substituted malonate compound from the substituted benzyl halide compound, which can be prepared by the conventional method, and the malonate compound, and the substituted malonate compound reacts with the phosphoric acid-containing compound to achieve hydrolysis, decarboxylation and cyclization in one step, thereby obtaining the indanone compound, simplifying the synthesis paths and saving the cost. The method is more suitable for batch production.

Description

technical field [0001] The invention relates to a preparation method of an organic compound, in particular to a preparation method of an indanone compound. Background technique [0002] Indanone 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] Indenone compounds can be used to synthesize indene compounds, and are further used to synthesize chiral anserometallocene catalyst components with very important three-dimensional structural properties. The catalyst components are composed of indene compounds or their derivative compounds and olefin polymerization Coordination of transition metal compounds with high performance. [0004] Changes in the coordination properties (such as changes in the substituents on the ligand) can lead to chang...

Claims

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Application Information

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IPC IPC(8): C07C49/633C07C45/46
Inventor 曹育才周慧马静君刘伟
Owner SHANGHAI RES INST OF CHEM IND
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