Hydroxyamine hydrochloride → 1-(2,6-Dihydroxy-4-methylphenyl)ethanone oxime

HRID 527517Notes

Reaction equation

HRID 527517 reaction equation
Cl.[NH2:2][OH:3].O.O.O.C([O-])(=O)C.[Na+].[OH:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([OH:20])[C:14]=1[C:21](=O)[CH3:22]>CCO.O.O>[OH:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([OH:20])[C:14]=1[C:21](=[N:2][OH:3])[CH3:22]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 104195313,5-Dihydroxy-4-acetyltoluene2×HCID 23665404Sodium Acetate Trihydrate2×

Product 1

HCID 1363786481-(2,6-Dihydroxy-4-methylphenyl)ethanone oximeYield 80.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent2×

Procedure

A solution of hydroxylamine hydrochloride (470 mg, 6.76 mmol) and sodium acetate trihydrate (590 mg, 4.34 mmol) dissolved in 20 ml of a mixture of EtOH/H2O (7/3) was added to a solution of 1-(2,6-dihydroxy-4-methylphenyl)ethanone (Intermediate 16, 940 mg) in 15 ml of a mixture of EtOH/H2O (7/3). After refluxing and stirring under N2 for 2 hours, additional hydroxylamine hydrochloride (159 mg, 2.29 mmol) and sodium acetate trihydrate (199 mg) dissolved in 5 ml of water were added. The reaction mixture was heated at reflux overnight. After cooling down to room temperature, the volatiles were removed. Water was added and the solid afforded was filtered, washed with water and dried giving 829 mg of the title compound.

Workup

  1. temperatureAfter refluxing
  2. additionwere added
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux overnight
  5. customthe volatiles were removed
  6. additionWater was added
  7. customthe solid afforded
  8. filtrationwas filtered
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-92275b4c70a94bdba1ce8048c8502061
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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