1,2-Dichloroethane → HCID 54185359, compound

HRID 2290972Notes

Reaction equation

HRID 2290972 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].Cl[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[N+:20]([O-:23])(O)=[O:21].[Cl:24]CCCl>>[Cl:24][C:12]1[CH:11]=[CH:10][C:6]([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:8])=[C:5]([N+:20]([O-:23])=[O:21])[C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 944Nitric AcidHCID 7964ChlorobenzeneHCID 8495Benzoyl chloride, 3-nitro-

Product 1

HCID 54185359HCID 54185359, compoundYield 93.2%

Conditions

Temperature
80 °C

Procedure

2.7 g (0.02 mol) of anhydrous ferric chloride was added to a mixture of 185.5 g (1.0 mol) of 3-nitrobenzoyl chloride and 124 g (1.1 mol) of chlorobenzene. While introducing nitrogen gas into the reactor, the reaction was conducted with stirring at a temperature of 140° to 150° C. for 19 hours. After the completion of the reaction, an excess amount of chlorobenzene was distilled at the same temperature under reduced pressure to recover it. Then the reaction mixture was cooled to 80° C. and 500 ml of 1,2-dichloroethane was added thereto to form a homogeneous solution. While keeping the temperature at 70° to 75° C., 335 g (5 mol) of 94% nitric acid (d =1.50) was added dropwise to the above solution over a period of two hours. After the completion of the addition, the reaction was continued at the reflux temperature of 1,2-dichloroethane for 12 hours to complete the nitration reaction. 1,2-Dichloroethane was distilled off to precipitate light brown particulate chlorodinitrobenzophenone. This product was recovered by filtration, washed with water, and dried to give 286 g (over-all yield 93.2%) of crude chlorodinitrobenzophenone.

Workup

  1. additionWhile introducing nitrogen gas into the reactor
  2. customAfter the completion of the reaction
  3. distillationan excess amount of chlorobenzene was distilled at the same temperature under reduced pressure
  4. customto recover it
  5. addition500 ml of 1,2-dichloroethane was added
  6. customto form a homogeneous solution
  7. customat 70° to 75° C.
  8. additionAfter the completion of the addition
  9. customthe nitration reaction
  10. distillation1,2-Dichloroethane was distilled off
  11. customto precipitate light brown particulate chlorodinitrobenzophenone
  12. filtrationThis product was recovered by filtration
  13. washwashed with water
  14. customdried

Sources & evidence

ORD record
ord-39c9fbe09c4f4e1eb38af0a70c133fd0
Source dataset
uspto-grants-1986_10
Patent number
US04618714

Reaction notes

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