2,5-Bis(2,2,2-trifluoroethoxy)nitrobenzene → 2,5-Bis(trifluoroethoxy)aniline

HRID 2412333Notes

Reaction equation

HRID 2412333 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:7][C:6]=1[N+:17]([O-])=O.[H][H]>[Ni].C(O)C>[F:1][C:2]([F:20])([F:21])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:7][C:6]=1[NH2:17]

Participants

5

Reactant 2

HCID 133704322,5-Bis(2,2,2-trifluoroethoxy)nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 133704342,5-Bis(trifluoroethoxy)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 59 g. (0.185 mole) of 2,5-bis-(2,2,2-trifluoroethoxy)nitrobenzene, about 15 g. of Raney nickel and 1200 ml. of ethanol is hydrogenated by shaking on a Parr hydrogenation apparatus with a hydrogen pressure of 40 to 50 p.s.i. for about five hours. The mixture is filtered, and the filtrate is evaporated to a liquid residue. The residue is distilled to provide 2,5-bis(2,2,2-trifluoroethoxy)aniline as a clear, colorless liquid, b.p. 95°-98° C./0.35 mm Hg.

Workup

  1. additionA mixture of 59 g
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated to a liquid residue
  4. distillationThe residue is distilled

Sources & evidence

ORD record
ord-cb5b1584e89e42daa74801acfc7a3be5
Source dataset
uspto-grants-1985_01
Patent number
US04491584

Reaction notes

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