Acetic Acid → N-tert-butylhydroxylammonium acetate

HRID 1636090Notes

Reaction equation

HRID 1636090 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-])[O-].[K+].[K+].C(O)(=O)C>O>[C:8]([O-:11])(=[O:10])[CH3:9].[C:2]([NH2+:6][OH:7])([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2777896N-tert-butylhydroxylamine hydrochloride

Product 1

HCID 86585825N-tert-butylhydroxylammonium acetateYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-tert-Butylhydroxylamine hydrochloride (56 g, 0.43 mol, 97%) was dissolved in water (226 g) and charged to a 1 L three-necked glass bottle under argon gas. Ethyl acetate (246 g) and potassium carbonate (79 g, 0.57 mol, 1.3 equiv.) were added and the mixture was stirred vigorously for 1 h at +20 ° C. Both phases were siphoned to a separating funnel. The water phase was separated off and extracted once more with ethyl acetate (100 ml). The organic phases were pooled and acetic acid (28.1 g, 0.47 mol, −1.09 equiv.) was added. The solvent was evaporated off. The resulting clear, yellow-green oil was treated with additional ethyl acetate (203 g) and concentrated again. The bottle was placed in the refrigerator and after 2 h the product had turned crystalline. The substance was easily crushed giving a slightly yellowish powder (63.4 g, 90%). This material could be recrystallised using either toluene or ethyl acetate as solvent. Differential scanning calorimetry showed an endothermic melting point at +67.7° C. Powder X-ray diffraction analysis showed a high degree of crystallinity.

Workup

  1. customBoth phases were siphoned to a separating funnel
  2. customThe water phase was separated off
  3. extractionextracted once more with ethyl acetate (100 ml)
  4. customThe solvent was evaporated off
  5. additionThe resulting clear, yellow-green oil was treated with additional ethyl acetate (203 g)
  6. concentrationconcentrated again
  7. waitThe bottle was placed in the refrigerator and after 2 h
  8. customThe substance was easily crushed

Sources & evidence

ORD record
ord-ffd824bcc59142158d153e7cee08fb81
Source dataset
uspto-grants-2003_01
Patent number
US06512143B1

Reaction notes

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