Water → 1-(2,4-Dihydroxy-3-propylphenyl)ethanone oxime

HRID 603405Notes

Reaction equation

HRID 603405 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=O)[CH3:13].Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+].O>CCO>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[N:16][OH:17])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 1363886031-(2,4-Dihydroxy-3-propylphenyl)ethanone oximeYield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2,4-dihydroxy-3-propylphenyl)ethanone (1.50 g, 7.72 mmol), hydroxylamine hydrochloride (1.61 g, 23.2 mmol), and anhydrous sodium acetate (1.90 g, 23.2 mmol) were combined in EtOH (30 mL) and stirred under reflux for 15 h. After cooling to rt, water (20 mL) was added, the EtOH was removed under reduced pressure and the aqueous phase was extracted with EtOAc (2×). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give 1.54 g (95%) of the title compound as a light-green solid. 1H NMR (400 MHz, CDCl3): δ 0.93 (t, 3H), 1.52 (m, 2H), 2.23 (s, 3H), 2.60 (t, 2H), 6.32 (d, 2H), 7.12 (d, 2H).

Workup

  1. temperatureunder reflux for 15 h
  2. customthe EtOH was removed under reduced pressure
  3. extractionthe aqueous phase was extracted with EtOAc (2×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f1ba6308d5c41e3ad5862a4a69de2e1
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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