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

HRID 1601749Notes

Reaction equation

HRID 1601749 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

400.0 g of 2,2-bis(3-nitro-4-hydroxyphenyl)hexafluoropropane and 1200 cc of methanol were put into a 2000-cc four-neck flask equipped with a thermometer, a Dimroth condenser and a stirrer, and stirred therein, to which was added 9.0 g (dry weight) of E196R/W5%Pd. This was heated and kept at 60 to 65° C. with stirring, to which was dropwise added 313.2 g of an aqueous solution of 60% hydrazine monohydrate over a period of 4 hours. After the aqueous hydrazine solution was added, the mixture was stirred for further 30 minutes, and then gradually cooled to room temperature. After the catalyst was removed through filtration, the reaction mixture was concentrated to obtain a crude product of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane. The crude yield was 336.8 g (98%). The purity in liquid chromatography was 97.9% (area %).

Workup

  1. customequipped with a thermometer
  2. additionto which was added
  3. dry with material9.0 g (dry weight) of E196R/W5%Pd
  4. temperatureThis was heated
  5. customkept at 60 to 65° C.
  6. stirringwith stirring, to which
  7. customof 4 hours
  8. additionAfter the aqueous hydrazine solution was added
  9. stirringthe mixture was stirred for further 30 minutes
  10. customAfter the catalyst was removed through filtration
  11. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-c06eb6fc8bd74f6a804d34be9daa10eb
Source dataset
uspto-grants-1999_11
Patent number
US05977413

Reaction notes

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