Chlorine → Benzenesulfonic acid, 3,5-dichloro-2-hydroxy-4-methyl-

HRID 259502

Reaction equation

HRID 259502 reaction equation
[S:1]([C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([CH3:12])=[CH:7][C:6]=1[OH:13])([OH:4])(=[O:3])=[O:2].[Cl:14]Cl>O.S(=O)(=O)(O)O>[S:1]([C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([CH3:12])=[C:7]([Cl:14])[C:6]=1[OH:13])([OH:4])(=[O:2])=[O:3]

Participants

5

Reactant 2

HCID 24526ChlorineHCID 110423235-Chloro-2-hydroxy-4-methylbenzenesulfonic acid

Product 1

HCID 3085507Benzenesulfonic acid, 3,5-dichloro-2-hydroxy-4-methyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

In a process for preparing 2-nitro-4,6-dichloro-5-methylphenol by sulfonation of 4-chloro-5-methylphenol to form 2-sulfo-4-chloro-5-methylphenol followed by chlorination of the 2-sulfo-4-chloro-5-methylphenol to 2-sulfo-4,6-dichloro-5-methylphenol with subsequent reaction of the 2-sulfo-4,6dichloro-5-methylphenol with nitric acid, the improvement which comprises carrying out the sulfonation at 40-100° C. with concentrated sulfuric acid to form 2-sulfo-4-chloro-5-methylphenol, thereafter diluting the reaction mixture with water to sulfuric acid content of 20 to 30 percent, chlorinating the resulting 2-sulfo-4-chloro-5-methylphenol with chlorine at 45-60° C. under a pressure of 1-3 bars gauge pressure to form 2-sulfo-4,6-dichloro-5-methylphenol.

Workup

  1. customat 45-60° C.

Sources & evidence

ORD record
ord-16070e9de4cb4eff9f6b0afde948090f
Source dataset
uspto-grants-1977_07
Patent number
US04038328

Linked notes

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