Water → 2-(but-3-en-1-yloxy)-N-hydroxyethanimine

HRID 217968Notes

Reaction equation

HRID 217968 reaction equation
S(O)(O)(=O)=O.[NH2:6][OH:7].C([O-])(=O)C.[Na+].O.[CH2:14]([O:18][CH2:19][CH:20]=O)[CH2:15][CH:16]=[CH2:17]>C(O)C>[CH2:14]([O:18][CH2:19][CH:20]=[N:6][OH:7])[CH2:15][CH:16]=[CH2:17]

Participants

6

Reactant 4

HCID 962Water2×HCID 159255Hydroxylamine, sulfate (1:1)HCID 517045Sodium AcetateHCID 57475674(But-3-en-1-yloxy)acetaldehyde

Product 1

HCID 722453722-(but-3-en-1-yloxy)-N-hydroxyethanimineYield 30.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine sulfate (20.5 g), sodium acetate (12.8 g) and water (20 ml) were added to a solution of 3-butenyloxyacetaldehyde (17.8 g; J. Chem. Soc., Perkin Trans. 1, 1999, 3143-3155) in ethanol (200 ml). The mixture was stirred at room temperature overnight and then water was added. The excess of ethanol was evaporated under reduced pressure and the resulting residue was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (6.20 g).

Workup

  1. customThe excess of ethanol was evaporated under reduced pressure
  2. extractionthe resulting residue was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2dfb3047b6694ac0a422faa6f6022ae1
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

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