Water → 1,1'-Oxybis(4-nitrobenzene)

HRID 1197139Notes

Reaction equation

HRID 1197139 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.[C:13](=[O:16])([O-])[O-].[K+].[K+].[OH2:19]>CS(C)=O.O.[N+](C1C=C(C=CC=1)C([O-])=O)([O-])=O.[Na+].[Na+].[N+](C1C=C(C=CC=1)C([O-])=O)([O-])=O>[CH:6]1[C:7]([N+:10]([O-:11])=[O:19])=[CH:8][CH:9]=[C:13]([O:16][C:4]2[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=2)[CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 74921,4-DinitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 75681,1'-Oxybis(4-nitrobenzene)Yield 92%

Reagents, catalysts & solvents 2

HCID 131717418Sodium 3-nitrobenzoate hemihydrateCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

1,4-Dinitrobenzene (3.52 g, 20.5 mmol), potassium carbonate (1.38 g, 10 mmol), and sodium 3-nitrobenzoate hemihydrate (32 mg, 0.16 mmol) were heated in dimethylsulfoxide (8 mL) at about 100° C. for approximately 5.8 hours. The reaction was allowed to cool and was poured into water (20 mL). The reaction vessel was rinsed with an additional 10 mL of water and the rinses were combined. The combined aqueous suspensions were allowed to stand overnight. The solid was collected, washed with water, and dried to give 2.51 g (92% pure) of 4,4'-dinitrodiphenyl ether.

Workup

  1. temperatureto cool
  2. washThe reaction vessel was rinsed with an additional 10 mL of water
  3. customThe solid was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-8b42172193f2485f88e78e6ea249967e
Source dataset
uspto-grants-1992_05
Patent number
US05117002

Reaction notes

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