Hydrochloric Acid → 4-(2,2,2-Trifluoroethoxy)aniline

HRID 3055

Reaction equation

HRID 3055 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1.C(O)C.Cl>O>[F:1][C:2]([F:14])([F:15])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27757691-Nitro-4-(2,2,2-trifluoroethoxy)benzene

Product 1

HCID 27771194-(2,2,2-Trifluoroethoxy)anilineYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a nitrogen atmosphere, 30.1 g (0.14 mol) of p-(2,2,2-trifluroethoxy) nitrobenzene, 82.1 g (1.47 mol) of reduced iron, 120 ml of ethanol and 40 ml of water were placed in a three-necked flask, to which 1.4 ml of concentrated hydrochloric acid was dropped under stirring and then refluxed for one hour. After cooling to a room temperature, it was separated by filtration, and the reaction solution was poured into iced water (about 2 liter), and precipitated solids were washed with water and then dried, to obtain 24.4 g (0.13 mol) of p-(2,2,2-trifluoroethoxy) aniline as pink solids. The yield was 94% and the melting point was 69.4° C.

Workup

  1. additionwas dropped
  2. temperaturerefluxed for one hour
  3. customit was separated by filtration
  4. additionthe reaction solution was poured into iced water (about 2 liter)
  5. customprecipitated solids
  6. washwere washed with water
  7. customdried

Sources & evidence

ORD record
ord-785e0a0408f94a47b06e9ceee5b1cfa9
Source dataset
uspto-grants-1998_03
Patent number
US05733481

Linked notes

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