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

HRID 1612463Notes

Reaction equation

HRID 1612463 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][C:8]1([CH3:15])[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1.Cl.[NH2:17][OH:18]>O.C(O)C>[CH3:7][C:8]1([CH3:15])[CH2:13][CH2:12][C:11](=[N:17][OH:18])[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 138166Cyclohexanone, 4,4-dimethyl-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 279448N-(4,4-dimethylcyclohexylidene)hydroxylamineYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium carbonate (10 g, 94.5 mmol) in water (30 ml) was added dropwise to a solution of 4,4-dimethylcyclohexanone (9.2 g, 73 mmol) and hydroxylamine hydrochloride (6.6 g, 94.5 mmol) in ethanol (50 ml) and water (60 ml). The resulting cloudy solution was heated at reflux for 2 h. Upon cooling the solvent volume was reduced (to remove most of the ethanol) and then extracted with ethyl acetate (2×). The organic layer was dried (MgSO4) and the solvent evaporated to afford the title compound (D52) (10 g).

Workup

  1. temperatureThe resulting cloudy solution was heated
  2. temperatureat reflux for 2 h
  3. temperatureUpon cooling the solvent volume
  4. customto remove most of the ethanol) and
  5. extractionthen extracted with ethyl acetate (2×)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-ef3b67a1a7354dba97bcd491e51c3048
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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