Sulfuric Acid → 3-(1-(Benzyloxyimino)ethyl)benzaldehyde

HRID 2296968Notes

Reaction equation

HRID 2296968 reaction equation
[CH2:1]([O:8][N:9]=[C:10]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#N)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].S(=O)(=O)(O)[OH:33]>C1(C)C=CC=CC=1>[CH2:1]([O:8][N:9]=[C:10]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:33])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 734333243-(1-(Benzyloxyimino)ethyl)benzonitrile

Product 1

HCID 734333173-(1-(Benzyloxyimino)ethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 24.15 g (95.0 mmol) of crude 3-(1-(benzyloxyimino)ethyl)benzonitrile in 1 liter of dry toluene was added 77.3 ml (116 mmol) of diisobutylaluminum hydride (1.5 mol/toluene solution) at −70° C. or below under an atmosphere of nitrogen, and the mixture was stirred overnight with gradually warming to room temperature. To the reaction mixture was added 200 ml of an about 20% aqueous solution of ammonium chloride, and the mixture was stirred at room temperature for 0.5 hours. Then, 400 ml of an about 5% aqueous solution of sulfuric acid was add thereto with ice-cooling. The mixture was stirred at the same temperature for 0.5 hours and then stirred at room temperature for 6 hours. The reaction mixture was separated and the aqueous layer was extracted with tert-butyl methyl ether. The organic layers were combined and washed twice with water, then dried and concentrated. The residue was subjected to silica gel column chromatography (eluted with n-hexane:toluene=1:1 and then 1:2) to obtain 18.26 g (72.1 mmol) of 3-(1-(benzyloxyimino)ethyl)benzoaldehyde.

Workup

  1. stirringthe mixture was stirred at room temperature for 0.5 hours
  2. temperaturewith ice-cooling
  3. stirringThe mixture was stirred at the same temperature for 0.5 hours
  4. stirringstirred at room temperature for 6 hours
  5. customThe reaction mixture was separated
  6. extractionthe aqueous layer was extracted with tert-butyl methyl ether
  7. washwashed twice with water
  8. customdried
  9. concentrationconcentrated
  10. washeluted with n-hexane

Sources & evidence

ORD record
ord-20040e7c293e42c0ac39aaf85cde3aee
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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