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

HRID 972674Notes

Reaction equation

HRID 972674 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 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

207 parts of 2,6-dichloro-4-nitroaniline is introduced into 1,800 parts of isopropanol and 18,000 parts of water; 700 parts of concentrated (98 wt%) sulfuric acid is then added. At 60° C., a solution of 140 parts of sodium nitrite in 240 parts of water is slowly run in. The mixture is cooled and suction filtered. There is obtained 190 parts (99% of theory) of 3,5-dichloronitrobenzene, m.p.: 61° - 62°.

Workup

  1. concentration700 parts of concentrated (98 wt%) sulfuric acid
  2. additionis then added
  3. customAt 60° C.
  4. temperatureThe mixture is cooled
  5. filtrationsuction filtered

Sources & evidence

ORD record
ord-90746420eabf4ec69265dfa1e5f51514
Source dataset
uspto-grants-1977_10
Patent number
US04053527

Reaction notes

Loading…