2',4'-Dihydroxyacetophenone → 2',4'-Dihydroxyacetophenone oxime

HRID 409314Notes

Reaction equation

HRID 409314 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[CH:8][C:9]=1[OH:10])=O.Cl.[NH2:13][OH:14].C([O-])(=O)C.[Na+]>O.O1CCOCC1>[OH:10][C:9]1[CH:8]=[C:7]([OH:11])[CH:6]=[CH:5][C:4]=1[C:2](=[N:13][OH:14])[CH3:1]

Participants

5

Reactant 3

HCID 69902',4'-DihydroxyacetophenoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 3451682',4'-Dihydroxyacetophenone oximeYield 43.6%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of 2,4-dihydroxyacetophenone (25 g, 0.16 mol), hydroxylamine hydrochloride (14.8 g, 0.21 mol), sodium acetate (20 g, 0.24 mol) and water/dioxane (300 mL, 1:1) was stirred at room temperature for three days before the mixture was partitioned between chloroform and water. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo and the residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane to give the title compound as a white solid (11.67 g): 1H NMR (CD3OD, 200 MHz): δ=7.26 (m, 1H), 6.28 (m, 2H), 4.88 (s, 2H), 3.29 (m, 1H), 2.24 (s, 3H).

Workup

  1. customwas partitioned between chloroform and water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-e2c77931a4474e6b84ee968dd0b60371
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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