Sulfuric Acid → 1-Chloro-3-nitrobenzene

HRID 972671Notes

Reaction equation

HRID 972671 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1N.C(O)(C)C.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]=[CH:5][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 84922-Chloro-4-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 84891-Chloro-3-nitrobenzeneYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

172.5 parts of 2-chloro-4-nitro-aniline are introduced into 180 parts of isopropanol and 300 parts of water, and 200 parts of concentrated sulfuric acid (98 percent strength by weight) 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. 142 parts (90% of theory) of 3-chloro-nitro-benzene, of melting point 40°-42° 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-bb2327d0a7014402a0420096593a1132
Source dataset
uspto-grants-1977_10
Patent number
US04053527

Reaction notes

Loading…