Cyclohexanone, 4,4-dimethyl- → N-(4,4-dimethylcyclohexylidene)hydroxylamine

HRID 1486455Notes

Reaction equation

HRID 1486455 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.Cl.[NH2:11][OH:12].C([O-])(=O)C.[Na+]>O.CCO.ClCCl>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[N:11][OH:12])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 138166Cyclohexanone, 4,4-dimethyl-HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 279448N-(4,4-dimethylcyclohexylidene)hydroxylamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 19096565Water ethanolSolvent

Procedure

A solution of 4,4-dimethylcyclohexanone (30 g, 0.238 mol), hydroxylamine hydrochloride (32.8 g, 0.476 mol) and sodium acetate (39.0 g, 0.476 mol) in H2O/EtOH (720 mL, 5/1) was heated under reflux. The reaction was monitored by TLC and cooled to room temperature upon completion. It was diluted with dichloromethane (500 mL). The organic layer was separated, washed with brine (100 mL) and dried over Na2SO4. Solvent was removed under reduced pressure, and 4,4-Dimethylcyclohexanone oxime was obtained as colorless solid, which was used in the next step without further purification.

Workup

  1. temperatureunder reflux
  2. customThe organic layer was separated
  3. washwashed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-be6a6a5df8144a6ca5494e5309426a17
Source dataset
uspto-grants-2016_08
Patent number
US09427479B2

Reaction notes

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