3-Nitro-1-phenylpropan-1-one → 1-Nitro-3-phenylpropane

HRID 1028878Notes

Reaction equation

HRID 1028878 reaction equation
[N+:1]([CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=O)([O-:3])=[O:2]>C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC>[N+:1]([CH2:4][CH2:5][CH2:6][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 5694913-Nitro-1-phenylpropan-1-one

Product 1

HCID 5623331-Nitro-3-phenylpropaneYield 88%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 12052TriethylsilaneSolvent

Procedure

Under an inert atmosphere, 3-nitro-1-phenylpropan-1-one (15) (12.5 g, 70.0 mmol) was dissolved in TFA (100 ml) and Et3SiH (30 ml). This mixture was stirred at room temperature under TLC and GC control. After reaction completion, the mixture was concentrated under reduced pressure and residue was distilled in vacuum to give 3-nitropropylbenzene (16) with 88% yield, bp. 120-123° C./4 mm.

Workup

  1. customAfter reaction completion
  2. concentrationthe mixture was concentrated under reduced pressure and residue
  3. distillationwas distilled in vacuum

Sources & evidence

ORD record
ord-062ef44d9e0e451ab10929db830d2b8f
Source dataset
uspto-grants-2014_05
Patent number
US08735627B2

Reaction notes

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