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

HRID 972672Notes

Reaction equation

HRID 972672 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.C(O)(C)C.[N+]([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 944Nitric AcidHCID 3776IsopropanolHCID 74302,6-Dichloro-4-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 12064Benzene, 1,3-dichloro-5-nitro-Yield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

207 parts of 2,6-dichloro-4-nitro-aniline are introduced into 500 parts of isopropanol, and 780 parts of 65 percent strength by weight nitric acid are then added to the mixture. A solution of 125 parts of NaNO2 in 175 parts of water is run in at 50° C., as described in Example 1. The mixture is cooled, 400 parts of water are added and the product is filtered off. 172 parts (90% of theory) of 3,5-dichloro-nitro-benzene, of melting point 55°-57° C., are obtained.

Workup

  1. additionare then added to the mixture
  2. customis run in at 50° C.
  3. temperatureThe mixture is cooled
  4. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-15e6aa4d348b49738d0af72b3ac1ea38
Source dataset
uspto-grants-1977_10
Patent number
US04053527

Reaction notes

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