1-Chloro-4-nitrobenzene → 1,1'-Oxybis(4-nitrobenzene)

HRID 637820

Reaction equation

HRID 637820 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11]([O-])(=O)[CH3:12].[K+].[C:16](=[O:19])([O-])[O-].[Na+].[Na+]>C(O)CCC>[CH:9]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[C:7]([O:19][C:16]2[CH:12]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 10340Sodium CarbonateHCID 517044Potassium Acetate

Product 1

HCID 75681,1'-Oxybis(4-nitrobenzene)

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
200 °C

Procedure

A 250 ml shaker bomb is charged with 79 g (0.50 mole) p-nitrochlorobenzene, 43 g n-butanol, 3 g (0.03 mole) potassium acetate, and 30 g (0.28 mole) sodium carbonate. The reactor is purged with nitrogen and heated to and maintained at 200° C. under autogenous pressure for 9 hours. No increase in pressure is observed and no 4,4'-dinitrodiphenyl ether is formed. This example illustrates that the reaction will not proceed using a protic solvent.

Workup

  1. customThe reactor is purged with nitrogen
  2. temperatureheated to and
  3. temperatureNo increase in pressure

Sources & evidence

ORD record
ord-75fdddeaadc445858041a462c4163a6b
Source dataset
uspto-grants-1985_12
Patent number
US04558164

Linked notes

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