Benzene, 1,1'-methylenebis[4-nitro- → n-hydroxy-1,1-bis(4-nitrophenyl)methanimine

HRID 376794Notes

Reaction equation

HRID 376794 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:20](C1C=CC(CC2C=CC([N+]([O-])=O)=CC=2)=CC=1)([O-])=[O:21].[N+](C1C=CC(C(C2C=CC([N+]([O-])=O)=CC=2)=O)=CC=1)([O-])=O>O.C(O)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[N:20][OH:21])[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 15753Benzene, 1,1'-methylenebis[4-nitro-HCID 86750897HCID 86750897, compound

Product 1

HCID 289708n-hydroxy-1,1-bis(4-nitrophenyl)methanimine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

The title compound was prepared by modification of procedures previously reported in the literature (Chapman and Fidler (1936) J. Chem. Soc, 448; Kulin and Leffek (1973) Can. J. Chem., 51: 687). A solution of chromic anhydride (20 g, 200 mmol) in 125 ml of H2O was added dropwise over 4 hours, to a suspension of bis(4-nitrophenyl)methane (25 g, 97 mmol) in 300 ml of acetic acid heated to reflux. The reaction mixture was heated at reflux for 1 hour, cooled to room temperature, and poured into water. The solid was collected by filtration, washed with H2O, 5% sodium bicarbonate, H2O, and air-dryed to provide a 1:1 mixture of bis(4-nitrophenyl)methane/4,4'-dinitrobenzophenone via 1H NMR. This material was oxidized with a second portion of chromic anhydride (20 g, 200 mmol), followed by an identical work-up procedure to provide the crude product. Trituration with 200 ml of benzene heated to reflux for 16 hours provided 4,4'-dinitrobenzophenone (20.8 g, 79%) as a yellow powder.

Workup

  1. temperatureheated to reflux
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 1 hour
  4. filtrationThe solid was collected by filtration
  5. washwashed with H2O, 5% sodium bicarbonate, H2O, and air-dryed
  6. customto provide
  7. customto provide the crude product

Sources & evidence

ORD record
ord-2a51b286dae24187a2bc92f73ba8351d
Source dataset
uspto-grants-2000_02
Patent number
US06022523

Reaction notes

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