Hydroxyamine hydrochloride → Ethyl 6-hydroxyimino-6-(2-naphthyl)hexanoate

HRID 2393169Notes

Reaction equation

HRID 2393169 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].O=[C:10]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>>[OH:3][N:2]=[C:10]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 18979220Ethyl 6-(naphthalen-2-yl)-6-oxohexanoate

Product 1

HCID 86753080Ethyl 6-hydroxyimino-6-(2-naphthyl)hexanoateYield 120.3%

Procedure

An ethanolic solution (150 ml) of ethyl 6-oxo-6-(2-naphthyl)hexanoate (15 g) was added to an aqueous solution (42 ml) of hydroxylamine hydrochloride (4.8 g) and sodium acetate (5.7 g) and the mixture was refluxed for 2 hours. The ethanol was then distilled off under reduced pressure and the residue was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried and the solvent was distilled off. The crude residue was purified by silica gel column chromatography (hexane-ethyl acetate =10:1) to provide ethyl 6-hydroxyimino-6-(2-naphthyl)hexanoate (19 g).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. distillationThe ethanol was then distilled off under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. customdried
  6. distillationthe solvent was distilled off
  7. customThe crude residue was purified by silica gel column chromatography (hexane-ethyl acetate =10:1)

Sources & evidence

ORD record
ord-cd6067a0d604440d9ab209dbfe09a2b7
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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