Ethanol → Benzene, 1,3-dichloro-5-nitro-

HRID 972667

Reaction equation

HRID 972667 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:5](N)=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.C(O)C.S(=O)(=O)(O)O.N([O-])=O.[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[C:7]([Cl:9])[CH:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 758932,4-Dichloro-6-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 12064Benzene, 1,3-dichloro-5-nitro-Yield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

207 parts of 4,6-dichloro-2-nitro-aniline are introduced into 400 parts of ethanol and 900 parts of water, and 400 parts of concentrated sulfuric acid (98 percent strength by weight) are then added to the mixture. A solution of 105 parts of NaNO2 in 175 parts of water is run in at 80° C., as described in Example 1. The mixture is cooled and the product is filtered off. 182 parts (95% 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. customis run in at 80° C.
  3. temperatureThe mixture is cooled
  4. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-c9bf08f38efb46f0987d460193911431
Source dataset
uspto-grants-1977_10
Patent number
US04053527

Linked notes

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