4-Aminophenol → Phenol, 4-[[2-nitro-4-(trifluoromethyl)phenyl]amino]-

HRID 128149

Reaction equation

HRID 128149 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.Cl[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[N+:20]([O-:22])=[O:21]>C(O)(C)C>[N+:20]([C:11]1[CH:12]=[C:13]([C:16]([F:17])([F:18])[F:19])[CH:14]=[CH:15][C:10]=1[NH:7][C:6]1[CH:5]=[CH:4][C:3]([OH:8])=[CH:2][CH:1]=1)([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene

Product 1

HCID 4771887Phenol, 4-[[2-nitro-4-(trifluoromethyl)phenyl]amino]-Yield 94.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6.0 g of p-aminophenol was dissolved in 60 ml of isopropyl alcohol. To the solution was added 6.0 g of 4-chloro-3-nitro-benzotrifluoride and the resulting solution was heated under reflux for 12 hours. After the reaction, the solvent was removed by distillation and the residue was dissolved in benzene. The resulting solution was filtered and the solvent was removed from the filtrate by distillation. Thus, 7.5 g of the desired product was obtained.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 12 hours
  3. customAfter the reaction
  4. customthe solvent was removed by distillation
  5. dissolutionthe residue was dissolved in benzene
  6. filtrationThe resulting solution was filtered
  7. customthe solvent was removed from the filtrate by distillation

Sources & evidence

ORD record
ord-6440437156744dc8be699e3c27fa2396
Source dataset
uspto-grants-1981_03
Patent number
US04259105

Linked notes

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