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

HRID 1601750Notes

Reaction equation

HRID 1601750 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.O.NN.NN>[Ni].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

6

Reactant 3

HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 111336832,2-Bis(3-nitro-4-hydroxyphenyl)hexafluoropropane2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

100.0 g of 2,2-bis(3-nitro-4-hydroxyphenyl)hexafluoropropane, 300 cc of methanol, and 5.0 g of developed NDT-90 (trade name, Raney nickel catalyst, manufactured by Kawaken Fine Chemical Co.) were put into a 500-cc four-neck flask equipped with a thermometer, a Dimroth condenser and a stirrer, and heated, with stirring, up to 60° C. to completely dissolve 2,2-bis(3-nitro-4-hydroxyphenyl)hexafluoropropane in the solvent. The resulting solution was kept at 60 to 65° C., to which was dropwise added 78.3 g of an aqueous solution of 60% hydrazine monohydrate over a period of 1 hour. 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-hydroxy-phenyl)hexafluoropropane. The crude yield was 82.5 g (96.0%). The purity in liquid chromatography was 96.5% (area %).

Workup

  1. customequipped with a thermometer
  2. temperaturea Dimroth condenser and a stirrer, and heated
  3. customwas kept at 60 to 65° C., to which
  4. customof 1 hour
  5. customAfter the catalyst was removed through filtration
  6. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-752f8180d40f45c19eea3de3e1ee3426
Source dataset
uspto-grants-1999_11
Patent number
US05977413

Reaction notes

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