Sulfuric Acid → Benzene, 1,3-dichloro-5-nitro-

HRID 972669Notes

Reaction equation

HRID 972669 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([Cl:12])[C:3]=1N.COCCO.S(=O)(=O)(O)O.N([O-])=O.[Na+]>O>[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([Cl:12])[CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 74302,6-Dichloro-4-nitroanilineHCID 80192-MethoxyethanolHCID 23668193Sodium Nitrite

Product 1

HCID 12064Benzene, 1,3-dichloro-5-nitro-Yield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

207 parts of 2,6-dichloro-4-nitro-aniline are introduced into 500 parts of glycol monomethyl ether and 1,000 parts of 50 percent strength by weight sulfuric acid are then added to the mixture. 90 parts of NaNO2 in 150 parts of water are added slowly at 70° C. The mixture is cooled and the product is filtered off. 179 parts (92% of theory) of 3,5-dichloro-nitro-benzene, of melting point 56°-59° C., are obtained.

Workup

  1. additionare then added to the mixture
  2. temperatureThe mixture is cooled
  3. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-cefd3258f3404d58bb2d44a989e26be1
Source dataset
uspto-grants-1977_10
Patent number
US04053527

Reaction notes

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