Method for synthetizing indanone compound

A synthesis method and technology of ketone compounds, which are applied in the field of preparation of organic compounds, can solve the problems of serious pollution and difficult operation, and achieve the effects of simple reaction operation, less environmental pollution, industrialization and sustainable development

Active Publication Date: 2012-06-13
SHANGHAI RES INST OF CHEM IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] In the methods provided by the above-mentioned documents, a large amount of aluminum trichloride or phosphoric acid-containing compounds are used, an

Method used

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  • Method for synthetizing indanone compound
  • Method for synthetizing indanone compound
  • Method for synthetizing indanone compound

Examples

Experimental program
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Embodiment 1

[0039] Add 600ml DMSO and 1mol sodium hydride into a 2L reaction flask, add dropwise a mixture of 1mol ethyl propionate and 1mol isobenzofuran-1(3H)-one under mechanical stirring, keep the reaction temperature at -10-0°C, drop After the addition was completed, the temperature was slowly raised to room temperature and the reaction was continued for 12 hours. After the reaction was completed, 800 ml of water was added to dilute, then extracted with n-hexane, and the solvent was distilled off to obtain 184.1 g of 1,3-dicarbonyl compound.

[0040] Dissolve the above-mentioned 184.1g dicarbonyl compound with 600ml ethylene dichloride, then add 2% mole catalyst iodine, and react with mechanical stirring for 14 hours. After the layer was washed once with water, the solvent was distilled off to obtain 111.6 g of 2-methyl-2,3-dihydro-1-indanone with a yield of 76.3%. The spectrogram data is as follows: 1 H NMR (500MHz, CDCl 3 ): δ=1.30(d, 3H), δ=2.54-2.76(d, 2H), δ=3.34-3.46(m, 1H), ...

Embodiment 2

[0042] Replace the isobenzofuran-1(3H)-one in Example 1 with an equimolar amount of 4,7-dimethyl-3-phenylisobenzofuran-1(3H)-one, and the other conditions are the same In Example 1, 196.3 g of 2,4,7-trimethyl-3-phenyl-2,3-dihydro-1-indanone was obtained, with a yield of 78.4%. The spectrogram data is as follows: 1 H NMR (300MHz, CDCl 3 ): δ=1.23(d, 3H), δ=2.34(s, 6H), δ=2.58-2.83(dd, 2H), δ=3.55(dd, 1H), δ=7.41-7.58(m, 5H) , δ=7.80(s, 1H).

Embodiment 3

[0044] The isobenzofuran-1(3H)-one in Example 1 is replaced with 5,7-dimethylisobenzofuran-1(3H)-one in an equimolar amount, and other reaction conditions are the same as in Example 1, 138.5 g of 2,5,7-trimethyl-2,3-dihydro-1-indanone was obtained with a yield of 79.5%. The spectrogram data is as follows: 1 H NMR (400MHz, CDCl 3 ): δ=1.27(d, 3H), δ=2.36(s, 3H), δ=2.58(s, 3H), δ=3.25(dd, 1H), δ=6.90(s, 1H), δ=7.04 (s, 1H).

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Abstract

The invention relates to a method for a synthetizing indanone compound, which comprises the steps of using substituted isobenzofuran-1(3H)-ketone as a raw material, reacting the substituted isobenzofuran-1(3H)-ketone and an ester compound containing alpha-methylene to produce a 1,3-dicarbonyl compound, and further synthetizing the substituted indanone compound under the action of a catalyst. Compared with the prior art, the problems including difficult operation due to large usage of acid compounds containing phosphorus or aluminium trichloride and the like, large amounts of liquid waste due to after-treatment and the like by means of the existing indanone compound synthetizing technology are mainly solved, reaction operation is simple, reaction conditions are easy to achieve, produced liquid waste is little in the after-treatment process, the pollution of the entire reaction process environment is low, and industrialization and sustainable development are easy to achieve.

Description

technical field [0001] The invention relates to a method for preparing organic compounds, in particular to a method for synthesizing indanone compounds. Background technique [0002] Indanones are important raw materials for metallocene catalysts for the synthesis of polyolefins, and are also widely used in pharmaceutical synthesis and fine chemicals. [0003] The main synthetic methods of indanone compounds reported in current literature (such as Organometallics 2006, 25, 1217-1229 and related literature and supporting information, US2007 / 0135595 A1, US2002 / 0077507 A1 and CN 101337874A) are: [0004] 1. Synthetic method using substituted aromatic hydrocarbon as starting material [0005] The method uses substituted aromatic hydrocarbons as starting materials, reacts with 2-substituted propionyl chloride under the catalysis of aluminum trichloride to generate substituted phenyl substituted ethyl ketone, and then undergoes bromination, aluminum trichloride catalyzed cyclizat...

Claims

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Application Information

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IPC IPC(8): C07C45/65C07C45/66C07C49/67C07C49/697C07C49/675C07C49/755
Inventor 周慧李永清王凡曹育才
Owner SHANGHAI RES INST OF CHEM IND
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