1-Indanone → 2,3-Dihydro-1H-inden-1-one oxime

HRID 1762746Notes

Reaction equation

HRID 1762746 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].[C:6]1(=O)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1>O.C(O)C>[C:6]1(=[N:2][OH:3])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 67351-IndanoneHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 3023232,3-Dihydro-1H-inden-1-one oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

In a 12 l four-necked flask fitted with a mechanical stirrer, a reflux condenser and a thermometer was placed 3.6 l of deionized water. Hydroxylamine hydrochloride was added. A clear, colorless solution formed (pH 2.5) to which was added 475 ml of 50% sodium hydroxide which had been diluted to 2.4 l with deionized water (pH 6.2). 1-Indanone was dissolved in 2.4 l of 3A anhydrous ethanol and added to the flask. The slightly turbid solution was heated at reflux for 15 minutes. A white solid started to precipitate at 39° C. The mixture was cooled to room temperature and then in an ice-water bath. The product was filtered off and washed with three 2 l portions of chilled water. The product was dried in a vacuum oven at 46° C. A white fluffy solid was obtained.

Workup

  1. customIn a 12 l four-necked flask fitted with a mechanical stirrer, a reflux condenser
  2. customA clear, colorless solution formed (pH 2.5) to which
  3. additionadded to the flask
  4. temperatureThe slightly turbid solution was heated
  5. temperatureat reflux for 15 minutes
  6. customto precipitate at 39° C
  7. filtrationThe product was filtered off
  8. washwashed with three 2 l portions of chilled water
  9. customThe product was dried in a vacuum oven at 46° C
  10. customA white fluffy solid was obtained

Sources & evidence

ORD record
ord-f0cf9e0ded0749a898ac8951915d67ad
Source dataset
uspto-grants-1989_05
Patent number
US04833273

Reaction notes

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