Sodium Hydroxide → 3,3-Dimethylindan-1-one oxime

HRID 222185Notes

Reaction equation

HRID 222185 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3]1.Cl.[NH2:14][OH:15].[OH-].[Na+]>CO.O>[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[N:14][OH:15])[CH2:3]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 3046283,3-Dimethyl-1-indanoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 866142543,3-Dimethylindan-1-one oximeYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,3-dimethylindan-1-one (1.16 g, 7.21 mmol) and hydroxylamine hydrochloride (1.31 g, 18.8 mmol) in MeOH (20.0 mL) was added a solution of sodium hydroxide (765 mg, 19.1 mmol) in water (10.0 mL). The mixture was heated to 80° C. for 2 h. The cooled reaction was concentrated in vacuo and partitioned between DCM and water. The organic layer was separated and concentrated in vacuo to afford the title compound as an oil (1.23 g, 97%). LC/MS: Rt=1.61 min, ES+ 176 (AA standard).

Workup

  1. customThe cooled reaction
  2. concentrationwas concentrated in vacuo
  3. custompartitioned between DCM and water
  4. customThe organic layer was separated
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-802a245a9a154b8a85e7196884e91751
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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