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Method for refining 4 ¿C (3,4 ¿C dichlorobenzene group) ¿C 1 ¿C tetralin ketone

A technology of dichlorophenyl and refining methods, applied in the separation/purification of carbonyl compounds, organic chemistry, etc., can solve problems such as unstable product quality, loss of materials and solvents, cumbersome refining process, etc., and achieve shortened production process time, The effect of stable product quality and short process time

Active Publication Date: 2007-10-10
DAQING PETROLEUM ADMINISTRATION +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] As can be seen from the relevant domestic and foreign literatures currently available, there is only a synthetic process for 4-(3,4-dichlorophenyl)-1-tetralone, and the currently commonly used refining method mainly adopts ethyl acetate, methyl ethyl ketone and cyclomethicone. A single solvent such as hexane is used as a refining solvent. If a product with a content greater than 99% is to be obtained, it must be refined many times. The refining process is cumbersome, which will also cause a large loss of materials and solvents, resulting in high production costs. The crude product with low content is refined and the quality of the product obtained is unstable

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] Embodiment 1, add 10 grams of 4-(3,4-dichlorophenyl)-1-tetralone with a content of 94.3% in a three-necked flask with stirring, add 10ml ethyl acetate and 30ml methyl tert-butyl base ether, heated to 60°C and refluxed for 2 hours, then the mother liquor was cooled to -5°C with frozen brine, and centrifuged to obtain a light yellow powder. The light yellow powder was recrystallized once again by the above method to obtain the refined product 4-(3,4-dichlorophenyl)-1-tetralone, and dried at 40°C for 24 hours to obtain the dry product 4-(3,4-dichlorophenyl) Phenyl)-1-tetralone 6.5g. Appearance is off-white powder, through liquid chromatography (chromatographic column: Shimadzu SHIM-PACK VP-ODS 4.6 * 150mm; Methanol: acetonitrile: potassium dihydrogen phosphate (40: 40: 20); Flow rate: 1.0ml / min. Ultraviolet detection wavelength : 214nm) to detect its purity as 98.7%.

Embodiment 2

[0010] Example 2, adding 10 grams of 4-(3,4-dichlorophenyl)-1-tetralone with a content of 94.3% in a three-necked flask with stirring, adding 25ml ethyl acetate and 5ml methyl tert-butyl base ether, heated to 100°C and refluxed for 0.5h, then the mother liquor was cooled to 10°C with ice water, and centrifuged to obtain a light yellow powder. The light yellow powder was recrystallized once again by the above method to obtain the refined product 4-(3,4-dichlorophenyl)-1-tetralone, and dried at 80°C for 24 hours to obtain the dry product 4-(3,4-dichlorophenyl) Phenyl)-1-tetralone 8.5g. Appearance is white powder, through liquid chromatography (column: Shimadzu SHIM-PACK VP-ODS 4.6 * 150mm; Methanol: acetonitrile: potassium dihydrogen phosphate (40: 40: 20); Flow rate: 1.0ml / min. Ultraviolet detection wavelength : 214nm) to detect its purity as 98.5%.

Embodiment 3

[0011] Example 3, adding 10 grams of 4-(3,4-dichlorophenyl)-1-tetralone with a content of 96.7% in a three-necked flask with stirring, adding 25ml ethyl acetate and 10ml methyl tert-butyl base ether, heated to 70°C and refluxed for 1h, then the mother liquor was cooled to 5°C with ice water, and centrifuged to obtain a light yellow powder. The light yellow powder was recrystallized once again by the above method to obtain the refined product 4-(3,4-dichlorophenyl)-1-tetralone, and dried at 50°C for 12 hours to obtain the dry product 4-(3,4-dichlorophenyl) Phenyl)-1-tetralone 8.4g. Appearance is light yellow powder, after liquid chromatography (chromatographic column: Shimadzu SHIM-PACK VP-ODS 4.6 × 150mm; methanol: acetonitrile: potassium dihydrogen phosphate (40: 40: 20); flow rate: 1.0ml / min. Ultraviolet detection Wavelength: 214nm) to detect its purity as 99.1%.

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Abstract

This invention discloses a method for refining 4-(3,4-dichlorophenyl)-1-tetralone. The method comprises: adding 4-(3,4-dichlorophenyl)-1-tetralone and solvent at a ratio of 1:(3-4) into a three-necked flask with a stirrer, heating under stirring until 4-(3,4-dichlorophenyl)-1-tetralone is completely dissolved, heating to 60-100 deg.C, refluxing for 0.5-2 h, cooling the filtrate to -5-10 deg.C, filtering, recrystallizing to obtain refined 4-(3,4-dichlorophenyl)-1-tetralone, and drying at 40-80 deg.C to obtain dry 4-(3,4-dichlorophenyl)-1-tetralone. The method has such advantages as high purity, short time, high yield, and stable product quality.

Description

Technical field: [0001] The invention relates to a method for refining fine chemical and pharmaceutical intermediates, in particular to a method for refining 4-(3,4-dichlorophenyl)-1-tetralone. Background technique: [0002] 4-(3,4-dichlorophenyl)-1-tetralone is also called 4-(3,4-dichlorophenyl)-3,4-dihydro-1-(2H)-naphthalenone, is Light yellow crystal, melting point 99℃~104℃, insoluble in water, easily soluble in organic solvents such as esters and aromatic compounds. It is an important intermediate in the synthesis of a large number of biological and pharmaceutical activities, especially for the synthesis of behavioral inhibitors with antidepressant effects. 4-(3,4-dichlorophenyl)-1-tetralone is an important intermediate in the synthesis of the new antidepressant sertraline hydrochloride, and sertraline hydrochloride accounts for 40% of the world antidepressant market. [0003] As can be seen from the relevant domestic and foreign literatures currently available, there ...

Claims

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Application Information

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IPC IPC(8): C07C49/693C07C49/67C07C45/81
Inventor 杨明庆刘杰张大伟于克利杨希志王俊峰李志男
Owner DAQING PETROLEUM ADMINISTRATION
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