Chromanone → 4H-1-Benzopyran-4-one, 2,3-dihydro-, oxime

HRID 1641374Notes

Reaction equation

HRID 1641374 reaction equation
C([O-])(=O)C.[Na+].[O:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=O)[CH2:8][CH2:7]1.Cl.[NH2:18][OH:19]>O.C(O)C>[O:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[N:18][OH:19])[CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 68110ChromanoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 44866984H-1-Benzopyran-4-one, 2,3-dihydro-, oximeYield 101.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of sodium acetate (41.53 g, 0.506 mol) in water at 60° C. was combined with a stirred mixture of chroman-4-one (25 g, 0.169 mol) and hydroxylamine hydrochloride (20.0 g, 0.287 mol) in ethanol at 60° C. The resulting mixture was heated at reflux for 90 minutes, cooled and filtered. The crude solid was washed with water to give chroman-4-one oxime (27.9 g, yield 96%), mp. 114-117° C., purity 95%.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 90 minutes
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe crude solid was washed with water

Sources & evidence

ORD record
ord-1fcb4e67d8664a97bb8864356f50bf95
Source dataset
uspto-grants-2012_02
Patent number
US08114991B2

Reaction notes

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