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

HRID 972673Notes

Reaction equation

HRID 972673 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>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

4

Reactant 2

HCID 3776IsopropanolHCID 74302,6-Dichloro-4-nitroaniline

Product 1

HCID 12064Benzene, 1,3-dichloro-5-nitro-Yield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

207 parts of 2,6-dichloro-4-nitroaniline is introduced into 300 parts of isopropanol and 9 parts of water; 200 parts of concentrated (98 wt%) sulfuric acid is then added to the mixture. At 50° C., 170 parts of isopropyl nitrite is run in, nitrogen being evolved. The mixture is cooled, 800 parts of water is added, and suction filtration carried out. There is obtained 188 parts (98% of theory) of 3,5-dichloronitrobenzene, m.p.: 59° - 62° C.

Workup

  1. concentration200 parts of concentrated (98 wt%) sulfuric acid
  2. additionis then added to the mixture
  3. customAt 50° C.
  4. temperatureThe mixture is cooled
  5. addition800 parts of water is added
  6. filtrationsuction filtration

Sources & evidence

ORD record
ord-dbb1323c0883492d952beb7853a6617d
Source dataset
uspto-grants-1977_10
Patent number
US04053527

Reaction notes

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