Water → (4-(4-Nitro-3-trifluoromethylphenoxy)phenyl]hexafluoropropane

HRID 37026

Reaction equation

HRID 37026 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](C2C=CC(O)=CC=2)([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.Cl[C:25]1[CH:26]=[CH:27][C:28]([N+:35]([O-:37])=[O:36])=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O>[N+:35]([C:28]1[CH:27]=[CH:26][C:25]([O:1][C:2]2[CH:3]=[CH:4][C:5]([CH:8]([C:9]([F:10])([F:11])[F:12])[C:13]([F:14])([F:15])[F:16])=[CH:6][CH:7]=2)=[CH:30][C:29]=1[C:31]([F:34])([F:33])[F:32])([O-:37])=[O:36]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 670525-Chloro-2-nitrobenzotrifluorideHCID 73864bisphenol AF

Product 1

HCID 131719010(4-(4-Nitro-3-trifluoromethylphenoxy)phenyl]hexafluoropropaneYield 95.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

16.0 g (47.6 mmol) of 2,2-bis(4-hydroxyphenyl)hexafluoropropane, 26.9 g (119 mmol) of 5-chloro-2-nitrobenzotrifluoride and 20.2 g (190 mmol) of sodium carbonate were reacted at 150° C. for 4 hours in 100 ml of dimethylformamide. After the reaction, the product was injected into 250 ml of iced water and extracted with ethyl acetate. The organic layer was washed with water and dried on anhydrous sodium sulfate. After filtration, the solvent was distilled off to recover a crude product, which was then purified by silica gel column chromatography (eluent: toluene/hexane=1/1) and then treated by activated carbon to obtain 32.6 g (yield: 95.9%) of 2,2-bis[(4-(4-nitro-3-trifluoromethylphenoxy)phenyl]hexafluoropropane.

Workup

  1. customAfter the reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. distillationthe solvent was distilled off
  7. customto recover a crude product, which
  8. customwas then purified by silica gel column chromatography (eluent: toluene/hexane=1/1)
  9. additiontreated by activated carbon

Sources & evidence

ORD record
ord-df0e5fe3d0d54a7e83f66d9783a23ae4
Source dataset
uspto-grants-1995_05
Patent number
US05419932

Linked notes

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