Hydroxyamine hydrochloride → 3-Benzyloxymethylcyclohexanone oxime

HRID 1956750Notes

Reaction equation

HRID 1956750 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][C:12](=O)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].Cl.[NH2:23][OH:24]>C(O)C>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][C:12](=[N:23][OH:24])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 138462513-[(Benzyloxy)methyl]cyclohexanone

Product 1

HCID 856315583-Benzyloxymethylcyclohexanone oximeYield 74.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound (11) (1.0 g; 4.6 mmol). in ethanol (25 ml), sodium acetate (0.754 g; 9.2 mmol) and hydroxylamine hydrochloride (0.384 g; 5.5 mmol) are added, and the resultant mixture is stirred at room temperature for 3 hours. The reaction mixture is poured into ice-water, extracted with chloroform, washed with water and dried. After concentration under reduced pressure, the residue is chromatographed on a silica gel column to give 3-benzyloxymethylcyclohexanone oxime (12) (0.8 g).

Workup

  1. extractionextracted with chloroform
  2. washwashed with water
  3. customdried
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue is chromatographed on a silica gel column

Sources & evidence

ORD record
ord-2be21dabb73641d183e8ff2c0b65b9ab
Source dataset
uspto-grants-1998_07
Patent number
US05780632

Reaction notes

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