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Method for preparing 1-aryl ethanesulfonic acid

A technology of arylethanesulfonic acid and arylhaloethane, which is applied in the field of preparation of 1-arylethanesulfonic acid, can solve the problem of unpleasant odor of mercaptan, difficulty in separation, and difficulty in 1-phenyl Ethanesulfonic acid, etc.

Inactive Publication Date: 2010-08-04
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first method is to prepare by substitution reaction of 1-phenylbromoethane and sulfite. The mixture of 1-phenylethanesulfonic acid and sulfite is directly obtained from the reaction, which is difficult to separate. The main problem of this method is It is difficult to obtain pure 1-phenylethanesulfonic acid
The second method is to prepare 1-phenylethanesulfonic acid by oxidation of 1-phenylethanethiol. This method can obtain pure 1-phenylethanesulfonic acid, but the mercaptan has a very unpleasant stench

Method used

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  • Method for preparing 1-aryl ethanesulfonic acid
  • Method for preparing 1-aryl ethanesulfonic acid
  • Method for preparing 1-aryl ethanesulfonic acid

Examples

Experimental program
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Embodiment 1

[0029] Add 55g (0.5mol) of sodium disulfide and 200mL of ethanol to a four-necked flask equipped with a stirrer, a condenser, and a thermometer, heat and stir until the sodium disulfide dissolves, then slowly add 185g (1mol) of 1-bromophenylethane dropwise. ). After the dropwise addition, the temperature was raised to reflux temperature for reaction, and the reaction was tracked by thin-layer chromatography until the end of the reaction. After the reaction was completed, the mixture was left standing to separate layers, and the organic layer was concentrated to obtain 1-phenylethyl disulfide, which weighed 123.3 g and had a yield of 90%.

[0030] Add 123.3g of 1-phenethyl disulfide to the three-necked flask, then add 162g of acetic acid, and add 50% H 2 o 2 200ml, stirred at room temperature, followed by TLC until the end of the reaction. 1-Phenylethanesulfonic acid was determined by HPLC to obtain 160.7 g, and the yield was 96%.

[0031] HPLC conditions: chromatographic c...

Embodiment 2

[0036] In a four-necked flask equipped with a stirrer, a condenser, and a thermometer, add 40 g (0.36 mol) of sodium disulfide and 40 g of water, heat and stir until the sodium disulfide is completely dissolved, then add 1.5 g of tetrabutylammonium bisulfate, slowly 135.05 g (0.73 mol) of 1-bromophenylethane was added dropwise. After the dropwise addition, the reaction was carried out at the reflux temperature, and the reaction was tracked by thin-layer chromatography until the end of the reaction. After the reaction was completed, it was extracted with petroleum ether, dried, filtered, and concentrated to obtain 89.0 g of 1-phenethyl disulfide, with a yield of 89%.

[0037] Add 89.0 g of 1-phenethyl disulfide to the three-necked flask, and add 5% KMnO dropwise at room temperature 4 2000.9g, the dropwise addition was completed, and the reaction was maintained at room temperature, and the reaction was tracked by thin-layer chromatography until the end of the reaction. 1-Pheny...

Embodiment 3

[0039] In a 250mL four-neck flask equipped with a stirrer, condenser, and thermometer, add 120.1g (0.5mol) of sodium sulfide (containing 9 crystal water), 9g (0.5mol) of water, heat and stir until the sodium sulfide is completely dissolved , add sulfur 16g (0.5mol), continue the reaction at reflux temperature for 1h, to obtain sodium disulfide solution.

[0040] Sodium disulfide solution was slowly added to a solution of 185 g (1 mol) of 1-bromophenylethane and 0.4 g of tetrabutylammonium bisulfate, and reacted at reflux temperature to generate 1-phenethyl disulfide. After the reaction was completed, the layers were separated, and the organic layer was 1-phenethyl disulfide to obtain 120.6 g. The yield was 88%.

[0041] Add 120.6g of 1-phenethyl disulfide to the three-necked flask, then add 212mL of acetic acid, add 50% H 2 o 2 239.4mL, stirred at room temperature for 12h, and the reaction ended. 1-phenylethanesulfonic acid was determined by HPLC to obtain 155.5 g, and the...

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Abstract

The invention relates to a method for preparing 1-aryl ethanesulfonic acid, which comprises: reacting 1-aryl halo ethane with sodium disulfide in a solvent under a refluxing condition to obtain diaryldisulfide; and performing the oxidizing reaction of the diaryldisulfide and an oxidant to obtain the 1-aryl ethanesulfonic acid. The method provided by the invention has the advantages of simple operation, low cost, high yield and high purity and belongs to the field of organic synthesis.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of 1-arylethanesulfonic acid. Background technique [0002] Optically pure 1-arylethanesulfonic acid has a chiral center and is a kind of strong acidic sulfonic acid resolution reagent. Since the artificially synthesized 1-arylethanesulfonic acid can be either a left-handed body or a right-handed body. Therefore, it is an excellent acidic resolution reagent to replace camphorsulfonic acid and camphorsulfonic acid derivatives in many aspects, and can be used for the resolution of compounds such as amino acids, basic drugs and basic intermediates. At present, the most researched 1-arylethanesulfonic acid is 1-phenylethanesulfonic acid. [0003] There are currently two main synthetic routes for 1-phenylethanesulfonic acid. The first method is to prepare by substitution reaction of 1-phenylbromoethane and sulfite. The mixture of 1-phenylethanesulfonic acid and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/16C07C309/24
Inventor 孙凤霞刘敬涛
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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