Trifluoroacetic acid → O-[2-(4-Chlorophenoxy)propyl]hydroxylamine

HRID 2292879Notes

Reaction equation

HRID 2292879 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH:7]([CH3:14])[CH2:8][O:9][N:10]=C(C)C)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH3:14])[CH2:8][O:9][NH2:10])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 157928292-Propanone, O-[2-(4-chlorophenoxy)propyl]oxime

Product 1

HCID 15239936O-[2-(4-Chlorophenoxy)propyl]hydroxylamineYield 768.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 g (4.13 mmol) of acetone O-[2-(4-chloro-phenoxy)-propyl]-oxime and 31 g of 30% strength aqueous trifluoroacetic acid solution were heated for 83/4 hours at 80° C. at a reduced pressure of 430 mbar, similarly to experiment 3b, 100 g of water being continuously added dropwise to the reaction mixture and a water/acetone mixture being distilled off. The working up similarly to 3b) gave 6.4 g of 2-(4-chlorophenoxy)-propoxyamine in this case. Yield: 76%.

Workup

  1. distillationa water/acetone mixture being distilled off

Sources & evidence

ORD record
ord-075400f6da3f4b989c956cf76c682acf
Source dataset
uspto-grants-1997_11
Patent number
US05684200

Reaction notes

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