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

HRID 62655

Reaction equation

HRID 62655 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[NH2:10][OH:11].Cl.C([O-])([O-])=O.[Na+].[Na+]>O.C(O)C>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[N:10][OH:11])[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)hydroxylamineYield 80.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To 4,4-Dimethylcyclohexanone (50 g, 396.19 mmol), NH2OH.HCl (35.84 g, 515.75 mmol) in H2O (190 mL) and ethanol (250 mL) was added a solution of Na2CO3 (54.16 g, 510.99 mmol) in water (170 mL) dropwise over a period of 20 minutes. After complete addition, reaction mixture was heated to reflux for 3h. The ethanol was evaporated, and the residue extracted into ethyl acetate (4×120 mL). The combined organic layer was washed with water (150 mL), brine (150 mL) and dried over sodium sulfate and concentrated to afford 45 g (80.4%) 4,4-dimethyl cyclohexanone oxime (I 6a) as white solid.

Workup

  1. additionAfter complete addition, reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 3h
  4. customThe ethanol was evaporated
  5. extractionthe residue extracted into ethyl acetate (4×120 mL)
  6. washThe combined organic layer was washed with water (150 mL), brine (150 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e03278eef4564eb4a7b51ecd215cd9c5
Source dataset
uspto-grants-2016_09
Patent number
US09447039B2

Linked notes

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