Chlorosulfonic acid → Benzenesulfonic acid,5-chloro-4-ethyl-2-hydroxy-

HRID 846458Notes

Reaction equation

HRID 846458 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:9][CH3:10].Cl[S:12]([OH:15])(=[O:14])=[O:13]>ClC1C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH2:9][CH3:10])=[CH:4][C:5]([OH:8])=[C:6]([S:12]([OH:15])(=[O:14])=[O:13])[CH:7]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 842234-Chloro-3-ethylphenol

Product 1

HCID 10857471Benzenesulfonic acid,5-chloro-4-ethyl-2-hydroxy-

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

In a 1-liter four-necked glass flask is prepared a solution mixture of 100 g of 4-chloro-3-ethylphenol and 200 g of monochlorobenzene. While the mixture is maintained at a temperature of 25°-30° C., 80 g of chlorosulfonic acid is added dropwise. After the mixture is maintained at the same temperature for 3 hours, the reaction mass of 5-chloro-4-ethyl-2-hydroxybenzenesulfonic acid is obtained and 75.1 g of acetic acid is added to the reaction mass. After 1.33 g of aluminium chloride and 0.67 g of sulfur chloride are added, 110 g of sulfuryl chloride is added dropwise. After the addition is completed, the temperature of the mixture is raised to 35° C. and the mixture is maintained at the temperature for 5 hours. In a 2-liter flask is charged 960 g of water, and the reaction mass is poured into the flask under stirring. The reaction mixture is separated into an aqueous layer and an oil layer, and the lower oil layer is removed to obtain aqueous solution of 3,5-dichloro-4-ethyl-2-hydroxybenzenesulfonic acid. After cooling to 20° C., 184 g of a 70% nitric acid solution is added dropwise, maintaining the temperature at 20°-25° C. After the addition is completed, the reaction mixture is heated to 45° C. and maintained at the temperature for 4 hours. The reaction mixture is cooled to 20° C. and filtered. The product is washed with water and dried to give 2,4-dichloro-3-ethyl-6-nitrophenol.

Workup

  1. customIn a 1-liter four-necked glass flask is prepared
  2. additionis added dropwise
  3. temperatureAfter the mixture is maintained at the same temperature for 3 hours

Sources & evidence

ORD record
ord-d004529801214a819c01a82e0f495bb5
Source dataset
uspto-grants-1992_08
Patent number
US05136109

Reaction notes

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