3-Phenylprop-2-Enal → 3-Phenyl-2-propenal oxime

HRID 1755767Notes

Reaction equation

HRID 1755767 reaction equation
[CH:1](=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(O)(O)(=O)=O.[NH2:16][OH:17].[OH-].[Na+]>O>[CH:1](=[N:16][OH:17])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)

Product 1

HCID 893693-Phenyl-2-propenal oximeYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
3 °C

Procedure

53.3 grams of cinnamaldehyde (0.40 mols) was added to a solution of 39.1 grams of hydroxylamine sulfate (0.48 mols) in 79.5 grams of water. The mixture was cooled in an icewater bath to 3° C. Then a solution of 17.7 grams of NaOH (0.44 mol) in 17.7 grams of water was added over a period of 25 minutes. The formed cinnamaldehyde oxime precipitated. The reaction mixture was warmed to roomtemperature and the crude product was filtered. After recrystallization from toluene pure cinnamaldehyde oxime was obtained as white crystals. Yield: 70%.

Workup

  1. customThe formed cinnamaldehyde oxime precipitated
  2. temperatureThe reaction mixture was warmed to roomtemperature
  3. filtrationthe crude product was filtered
  4. customAfter recrystallization from toluene pure cinnamaldehyde oxime
  5. customwas obtained as white crystals

Sources & evidence

ORD record
ord-2c2398847e87477f8173092a73d0ae91
Source dataset
uspto-grants-1995_08
Patent number
US05438143

Reaction notes

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