Water → Phenyl (aminooxy)acetate

HRID 251155Notes

Reaction equation

HRID 251155 reaction equation
[C:1]1([O:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[O:12]([NH2:14])[CH3:13].C([O-])([O-])=O.[K+].[K+].O>CCOCC>[O:7]([C:8]([CH2:13][O:12][NH2:14])=[O:9])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 45091051Phenyl (aminooxy)acetateYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Phenylchloroformate (14.78 g, 94.4 mmol) was dissolved in Et2O (375 mL) and methoxylamine hydrochloride (7.88 g, 94.4 mmol), K2CO3 (15.66 g, 113.3 mmol), and water (18 mL) were added and the solution stirred over 64 hours. Solids were filtered, the phases separated, and the organic component concentrated under reduced pressure. The crude liquid was purified by column chromatography with silica gel (1:4 EtOAc/hexanes) to afford N-(phenoxycarbonyl)methoxylamine as a white solid (14.18 g, 90%).

Workup

  1. filtrationSolids were filtered
  2. customthe phases separated
  3. concentrationthe organic component concentrated under reduced pressure
  4. customThe crude liquid was purified by column chromatography with silica gel (1:4 EtOAc/hexanes)

Sources & evidence

ORD record
ord-683d20632a4147359c17b1d75a83c2c4
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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