2,4,4'-Trihydroxybenzophenone → (2,4-Dihydroxyphenyl)(4-hydroxyphenyl)methanone Oxime

HRID 1816405Notes

Reaction equation

HRID 1816405 reaction equation
C([O-])(=O)C.[Na+].[OH:6][C:7]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:8]=1[C:14]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=O.Cl.[NH2:24][OH:25].O.[Cl-].[Na+].O>O.C(O)C>[OH:6][C:7]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:8]=1[C:14]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[N:24][OH:25]

Participants

7

Reactant 4

HCID 738522,4,4'-TrihydroxybenzophenoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 23713072Sodium chloride dihydrate

Product 1

HCID 136342142(2,4-Dihydroxyphenyl)(4-hydroxyphenyl)methanone OximeYield 48%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium acetate (0.46 g, 5.57 mmol) in water (3 mL) was added into a mixture of (2,4-dihydroxyphenyl)(4-hydroxyphenyl)methanone (0.91 g, 3.97 mmol), hydroxylamine hydrochloride (0.36 g, 5.17 mmol), and ethanol (20 mL). The reaction mixture was refluxed for 2 days. The mixture was poured into water/brine and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography CH2Cl2/EtOAc/MeOH 20/10/1) gave a white solid (0.46 g, 48% yield); MS m/e 245 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 days
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customEvaporation and purification by flash chromatography CH2Cl2/EtOAc/MeOH 20/10/1)

Sources & evidence

ORD record
ord-05755b58564f47fbb48aad90f2af275f
Source dataset
uspto-grants-2005_04
Patent number
US06884814B2

Reaction notes

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