2',6'-Dihydroxyacetophenone → 1-(2,6-Dihydroxyphenyl)ethanone oxime

HRID 527511Notes

Reaction equation

HRID 527511 reaction equation
Cl.[NH2:2][OH:3].O.O.O.C([O-])(=O)C.[Na+].[OH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:14]=1[C:20](=O)[CH3:21]>CCO.O.O>[OH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:14]=1[C:20](=[N:2][OH:3])[CH3:21]

Participants

6

Reactant 3

HCID 696872',6'-DihydroxyacetophenoneHCID 443297Hydroxyamine hydrochloride2×HCID 23665404Sodium Acetate Trihydrate2×

Product 1

HCID 1363786461-(2,6-Dihydroxyphenyl)ethanone oxime

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent3×

Procedure

A solution of hydroxylamine hydrochloride (756 mg, 10.9 mmol) and sodium acetate trihydrate (1.71 g, 12.6 mmol) dissolved in 23 ml of a mixture of EtOH/H2O (7/3) was added to a solution of 2′,6′-dihydroxyacetophenone (1.5 g, 9.9 mmol) in 12 ml of a 7/3 EtOH/H2O mixture. After refluxing and stirring under N2 for 2 hours, additional hydroxylamine hydrochloride (340 mg, 4.9 mmol) and sodium acetate trihydrate (570 mg, 4.19 mmol) dissolved in 7 ml of water were added and the reflux was continued for additional 30 minutes. After cooling down to room temperature, the volatiles were removed. Then water was added and the solid obtained was filtered, washed with water and dried. This afforded 1.3 g of the title compound.

Workup

  1. temperatureAfter refluxing
  2. additionwere added
  3. waitthe reflux was continued for additional 30 minutes
  4. customthe volatiles were removed
  5. additionThen water was added
  6. customthe solid obtained
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-2adedf9f54ba431b90d0741427f5401f
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

Loading…