Sodium Hydroxide → (+,-) 2-Phenyl-cyclopentanone oxime

HRID 989479Notes

Reaction equation

HRID 989479 reaction equation
[C:1]1([CH:7]2[CH2:11][CH2:10][CH2:9][C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:13].[Na+].Cl.[NH2:16]O>C(O)C.O>[C:1]1([CH:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[N:16][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2901542-PhenylcyclopentanoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 72517452(+,-) 2-Phenyl-cyclopentanone oximeYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Scheme IA, step A: 2-Phenyl-cyclopentanone (prepared according to R. Sudha et. al. J. Org. Chem., 61, 1877-1879, 1996) (1.0 g, 6.2 mmol) was dissolved in 20 mL of absolute ethanol. To this solution was added sodium hydroxide (0.5 g, 12.5 mmol) dissolved in 10 mL water followed by hydroxylamine hydrochloride (0.65 g, 9.36 mmol) and stirred overnight at room temperature. The reaction was diluted with water and the precipitate collected by filtration. The white solid was vacuum oven-dried at 35° C. for 30 minutes to give 0.75 g (69%) of the title compound. The NMR was consistent with the assigned structure.

Workup

  1. filtrationthe precipitate collected by filtration
  2. customoven-dried at 35° C. for 30 minutes

Sources & evidence

ORD record
ord-e6f32b8e53cd473d8bb9c7325669c9cb
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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