Ethanol → (2-Methyl-3-butenyloxy)acetaldehyde oxime

HRID 217978Notes

Reaction equation

HRID 217978 reaction equation
[CH2:1](O)[CH3:2].[C:4]([O-])(=O)C.[Na+].S(O)(O)(=O)=O.[NH2:14][OH:15].[Cl-].[Na+].[C:18]([O:21][CH2:22][CH3:23])(=O)[CH3:19]>C(O)=O.O.O>[CH3:4][CH:19]([CH:1]=[CH2:2])[CH2:18][O:21][CH2:22][CH:23]=[N:14][OH:15]

Participants

8

Reactant 5

HCID 702EthanolHCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 159255Hydroxylamine, sulfate (1:1)HCID 517045Sodium Acetate

Product 1

HCID 72245408(2-Methyl-3-butenyloxy)acetaldehyde oxime

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18673298Formic acid--water (1/1)Solvent

Procedure

A solution of the compound obtained in Preparation Example 9-(1) (4.92 g) in formic acid/water (20 mL/5 mL) was stirred at room temperature for 16 hours. Ethanol (30 mL), water (10 mL), sodium acetate (4.63 g) and hydroxylamine sulfate (4.63 g) were added to the reaction solution, and the mixture was stirred at room temperature for eight hours. Saturated aqueous sodium chloride and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was washed again with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (1.57 g).

Workup

  1. stirringthe mixture was stirred at room temperature for eight hours
  2. customthe organic layer was separated
  3. washThe organic layer was washed again with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e5f5bf0b7ee24edea2f42357d14b50db
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

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