Ethyl Acetate → N-tert-butylhydroxylammonium acetate

HRID 1636091Notes

Reaction equation

HRID 1636091 reaction equation
Cl.[C:2]([NH:6][OH:7])([CH3:5])([CH3:4])[CH3:3].[C:8]([O:11]CC)(=[O:10])[CH3:9].C([O-])(=O)C.[Na+]>O>[C:8]([O-:11])(=[O:10])[CH3:9].[C:2]([NH2+:6][OH:7])([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 2777896N-tert-butylhydroxylamine hydrochloride

Product 1

HCID 86585825N-tert-butylhydroxylammonium acetateYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-tert-Butylhydroxylamine hydrochloride (19.7 g, 98%, 0.15 mol) was dissolved in water (40 g) at +20° C. Ethyl acetate (118 g) and sodium acetate (19.3 g, 0.24 mol, 1.5 equiv.) were added. A slurry was formed initially but then dissolved. After 2 h the bluish organic phase was separated and concentrated giving an opaque, yellow oil (20.6 g, 88%) that solidified upon standing in the refrigerator. Chromatographic purity (GC): 97.0 area %.

Workup

  1. customA slurry was formed initially
  2. dissolutiondissolved
  3. customAfter 2 h the bluish organic phase was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ec4b8878f40d4818a52cb826f4c8755c
Source dataset
uspto-grants-2003_01
Patent number
US06512143B1

Reaction notes

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