Nitric Acid → Phenol, 2,4-dichloro-3-methyl-6-nitro-

HRID 259497

Reaction equation

HRID 259497 reaction equation
ClC1C(C)=CC(O)=CC=1.[S:10]([C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([CH3:21])=[CH:16][C:15]=1[OH:22])([OH:13])(=[O:12])=[O:11].S([C:27]1[CH:32]=[C:31]([Cl:33])[C:30]([CH3:34])=[C:29]([Cl:35])[C:28]=1[OH:36])(O)(=O)=O.[N+:37]([O-])([OH:39])=[O:38].S(=O)(=O)(O)O>>[N+:37]([C:27]1[CH:32]=[C:31]([Cl:33])[C:30]([CH3:34])=[C:29]([Cl:35])[C:28]=1[OH:36])([O-:39])=[O:38].[S:10]([C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([CH3:21])=[CH:16][C:15]=1[OH:22])([OH:13])(=[O:11])=[O:12]

Participants

7

Reactant 5

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 17324-Chloro-3-methylphenolHCID 3085507Benzenesulfonic acid, 3,5-dichloro-2-hydroxy-4-methyl-HCID 110423235-Chloro-2-hydroxy-4-methylbenzenesulfonic acid

Product 2

HCID 170222Phenol, 2,4-dichloro-3-methyl-6-nitro-HCID 110423235-Chloro-2-hydroxy-4-methylbenzenesulfonic acid

Procedure

2-NITRO-4,6-DICHLORO-5-METHYLPHENOL IS PREPARED BY THE SULFONATION OF 4-CHLORO-5-METHYLPHENOL TO FORM 2-SULFO-4-CHLORO-5-METHYLPHENOL WHICH IS CHLORINATED TO 2-SULFO-4,6-DICHLORO-5-METHYLPHENOL WHICH IS IN TURN REACTED WITH NITRIC ACID TO FORM THE DESIRED PRODUCT. The sulfonation is carried out with concentrated sulfuric acid at elevated temperatures to form 2-sulfo-4-chloro-5-methylphenol. Thereafter the reaction mixture is diluted with water to a sulfuric acid content of 20-30%. The resulting 2-sulfo-4-chloro-5-methylphenol is chlorinated with chlorine at elevated temperature and normal or elevated pressures to form 2-sulfo-4,6-dichloro-5-methylphenol which is then reacted with nitric acid.

Sources & evidence

ORD record
ord-8f514fe2b26543cfad44a0bd46bdb41c
Source dataset
uspto-grants-1977_07
Patent number
US04038328

Linked notes

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