Cyclohexyl phenyl ketone → Cyclohexyl-phenyl-methanone oxime

HRID 271838

Reaction equation

HRID 271838 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH:9]1([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>CO>[CH:9]1([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:2][OH:3])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 12837Cyclohexyl phenyl ketoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 346900Cyclohexyl-phenyl-methanone oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxylamine hydrochloride (0.48 g, 6.7 mMol) and sodium acetate (1.4 g, 10.2 mMol) were added to a round bottom flask containing cyclohexyl-phenyl-methanone Compound 18a (0.97 g, 5.1 mMol) in MeOH (30 mL) at r.t. The mixture was stirred at r.t. for 15 hrs. The solvent was removed in vacuo and the residue was extracted with CH2Cl2. The organic layer was sequentially washed with a saturated solution of NaHCO3, then brine. The organic layer was dried over Na2SO4, decanted and the solvent removed in vacuo to provide cyclohexyl-phenyl-methanone oxime Compound 18b (1.0 g) as a white solid, which was used in the next step without purification. MS m/z 204 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. extractionthe residue was extracted with CH2Cl2
  3. washThe organic layer was sequentially washed with a saturated solution of NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customdecanted
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-83d6825bf7914461b78e20bc77d4d6a9
Source dataset
uspto-grants-2008_11
Patent number
US07452997B2

Linked notes

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