4-Aminophenol → 4-[2,6-Dichloro-4-(trifluoromethyl)phenoxy]aniline

HRID 1679241Notes

Reaction equation

HRID 1679241 reaction equation
[OH-].[K+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[C:17]([Cl:19])[C:16](Cl)=[C:15]([Cl:21])[CH:14]=1>O.CS(C)=O>[Cl:19][C:17]1[CH:18]=[C:13]([C:12]([F:11])([F:22])[F:23])[CH:14]=[C:15]([Cl:21])[C:16]=1[O:10][C:7]1[CH:8]=[CH:9][C:4]([NH2:3])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 4034-AminophenolHCID 14797Potassium HydroxideHCID 27333991,2,3-Trichloro-5-(trifluoromethyl)benzene

Product 1

HCID 203620974-[2,6-Dichloro-4-(trifluoromethyl)phenoxy]aniline

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

32.5 g of potassium hydroxide flakes in 30 ml of water were added to 54.5 g (0.5 mole) of 4-aminophenol dissolved in 350 ml of dimethylsulfoxide, and 150 ml of a water/dimethylsulfoxide mixture were distilled off in vacuo at 15-20 mm Hg. 125 g (0.5 mole) of 1-trifluoromethyl-3,4,5-trichlorobenzene [nD20 : 1.5008 67- 68% of theory, compare J. Am. Chem. Soc. 57, 2066-2068 (1935) and U.S. Pat. No. 2,654,789] were then added to the reaction mixture at about 70°-80° C and the mixture was stirred for a further 2 hours at 120°-130° C. The substance was precipitated with water, filtered off, washed with water and recrystallized moist from an ethanol/water mixture, thus giving 40-50% of theory of 4-(2,6-dichloro-4-trifluoromethylphenoxy)-aniline of melting point 128°-130° C.

Workup

  1. distillation150 ml of a water/dimethylsulfoxide mixture were distilled off in vacuo at 15-20 mm Hg
  2. addition2,654,789] were then added to the reaction mixture at about 70°-80° C
  3. customThe substance was precipitated with water
  4. filtrationfiltered off
  5. washwashed with water
  6. customrecrystallized moist from an ethanol/water mixture

Sources & evidence

ORD record
ord-9f7380e6b30646d6b675cb3377376abe
Source dataset
uspto-grants-1978_03
Patent number
US04080193

Reaction notes

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