Hydroxyamine hydrochloride → Ethyl 2-(4-(1-(hydroxyimino)propyl)phenoxy)acetate

HRID 68306

Reaction equation

HRID 68306 reaction equation
[C:1]([C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=1)(=O)[CH2:2][CH3:3].Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+]>CO.O>[OH:20][N:19]=[C:1]([C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 24693252Ethyl 2-(4-propionylphenoxy)acetate

Product 1

HCID 86699619Ethyl 2-(4-(1-(hydroxyimino)propyl)phenoxy)acetateYield 76.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of the product of step 1 (49 g, 0.2076 moles) in methanol (343 ml), hydroxylamine hydrochloride (28.6 g, 0.4152 moles) and a solution of sodium acetate (34 g, 0.4152 moles) in water (147 ml) were added and the reaction mixture was refluxed for 1 hour. The solvents were evaporated under reduced pressure. The residue was dissolved in water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evapourated under reduced pressure to yield 40 gm (76%) of product as solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 1 hour
  2. customThe solvents were evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with ethyl acetate
  5. extractionThe combined ethyl acetate extract
  6. washwas washed with water & brine
  7. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-bac0e94301054ed7a1dca8242b51a003
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Linked notes

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