2,2-Bis(3-nitro-4-hydroxyphenyl)hexafluoropropane → 2,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane

HRID 1601748Notes

Reaction equation

HRID 1601748 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([N+:27]([O-])=O)[CH:21]=2)([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13])[CH:7]=[CH:8][C:9]=1[OH:10])([O-])=O>CO>[NH2:27][C:22]1[CH:21]=[C:20]([C:11]([C:6]2[CH:7]=[CH:8][C:9]([OH:10])=[C:4]([NH2:1])[CH:5]=2)([C:12]([F:13])([F:14])[F:15])[C:16]([F:17])([F:18])[F:19])[CH:25]=[CH:24][C:23]=1[OH:26]

Participants

3

Reactant 1

HCID 111336832,2-Bis(3-nitro-4-hydroxyphenyl)hexafluoropropane

Product 1

HCID 6326032,2-Bis(3-amino-4-hydroxyphenyl)hexafluoropropane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15.0 g of 2,2-bis(3-nitro-4-hydroxyphenyl)hexafluoropropane and 50.0 cc of methanol were put into a 100-cc four-neck flask equipped with a thermometer, a Dimroth condenser and a stirrer, and stirred therein, to which was added 0.23 g (dry weight) of E196R/W5%Pd (trade name, 5% palladium-carbon catalyst, manufactured by Degussa Japan Co.). This was heated and kept at 60 to 65° C., to which was dropwise added 11.8 g of an aqueous solution of 60% hydrazine monohydrate over a period of 20 minutes. If desired, the reaction system was cooled, as generating heat during the reaction. After the aqueous hydrazine solution was added, the mixture was stirred at 70° C. for 30 minutes, and then gradually cooled to room temperature. After the catalyst was removed through filtration, methanol and water were evaporated out of the reaction mixture to obtain a crude product of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane. The crude yield was 12.6 g (98%). The purity in liquid chromatography was 98.3% (area %).

Workup

  1. customequipped with a thermometer
  2. additionto which was added
  3. dry with material0.23 g (dry weight) of E196R/W5%Pd (trade name, 5% palladium-carbon catalyst, manufactured by Degussa Japan Co.)
  4. temperatureThis was heated
  5. customkept at 60 to 65° C., to which
  6. customof 20 minutes
  7. temperaturethe reaction system was cooled
  8. temperatureas generating heat during the reaction
  9. additionAfter the aqueous hydrazine solution was added
  10. stirringthe mixture was stirred at 70° C. for 30 minutes
  11. customAfter the catalyst was removed through filtration, methanol and water
  12. customwere evaporated out of the reaction mixture

Sources & evidence

ORD record
ord-cc1ba78dcbd5414ea3d2e072619b26bd
Source dataset
uspto-grants-1999_11
Patent number
US05977413

Reaction notes

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