Sodium Carbonate → N-(4,4-dimethylcyclohexylidene)hydroxylamine

HRID 471798

Reaction equation

HRID 471798 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-])[O-].[Na+].[Na+]>C(O)C.O>[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 10340Sodium CarbonateHCID 138166Cyclohexanone, 4,4-dimethyl-HCID 443297Hydroxyamine hydrochloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 4,4-dimethylcyclohexanone (3.0 g, 0.024 mole) and hydroxylamine hydrochloride (2.2 g, 0.031 mole) in ethanol (15 mL) and water (20 mL) at room temperature was added a solution of sodium carbonate (3.3 g, 0.031 mol) in water (10 mL), dropwise. The mixture was heated under reflux for 3 hr, cooled to room temperature and ethanol was removed in vacuo. The aqueous residue was extracted several times with ethyl acetate, combined extracts were dried over MgSO4 and concentrated in vacuo affording the title compound as a white solid, used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93 (s, 6H), 1.28 (t, J=6.6 Hz, 2H), 1.35 (t, J=6.6 Hz, 2H), 2.11 (t, J=6.6 Hz, 2H), 2.36 (t, J=6.6 Hz, 2H), 10.12 (s, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. customethanol was removed in vacuo
  4. extractionThe aqueous residue was extracted several times with ethyl acetate
  5. dry with materialwere dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0bfd4e52f284fbfa785d704796fd699
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Linked notes

Loading…