Water → HCID 3613323, compound

HRID 240539Notes

Reaction equation

HRID 240539 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9](=O)[CH3:10].Cl.[NH2:13][OH:14].C(OCC)(=O)C.O>C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9](=[N:13][OH:14])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 102792-AcetylhydroquinoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 3613323HCID 3613323, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(2,5-dihydroxyphenyl)ethanone (10.0 g, 65.73 mmol) in ethanol (200 mL) was added hydroxylamine hydrochloride (13.7 g, 197.2 mmol). After heating to reflux for 16 hours, the solvent was reduced under reduced pressure. Ethyl acetate (200 mL) and water were added and the mixture was extracted with ethyl acetate (3×). The combined organic layers were dried and concentrated to provide the product (10 g, 91%) as yellow solid.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 16 hours
  3. extractionthe mixture was extracted with ethyl acetate (3×)
  4. customThe combined organic layers were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b5f4c399165434f9b6be6238f85996f
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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