Benzaldehyde → (Z)-Benzaldehyde oxime

HRID 1608042Notes

Reaction equation

HRID 1608042 reaction equation
S(O)(O)(=O)=O.[NH2:6][OH:7].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CO.[OH-].[Na+]>C(O)(=O)C.O>[CH:8](=[N:6][OH:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 887MethanolHCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)

Product 1

HCID 12143(Z)-Benzaldehyde oximeYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

943 g. (5.75 moles) of hydroxylamine sulfate are placed in a 12 liter flask with 1166 g. (11 moles) of benzaldehyde, 250 ml. of methanol and 5900 ml. of water. The mixture is stirred and chilled to 10° C. in an ice bath. Add 960 g. (12 mole) of 50% sodium hydroxide is added to the mixture gradually over a period of one hour while the temperature of the mixture is maintained below 25° C. with cooling. The mixture is stirred until the reaction is complete (approximately one hour). The mixture is neutralized to pH 7.0 with acetic acid. The lower oxime layer is separated and the aqueous layer is extracted with 2 liters of toluene. The oxime layer and toluene extract are washed twice with 1 liter of water. The toluene is stripped and 1307 g. of the oxime at 98% purity for a 95% yield is obtained.

Workup

  1. additionAdd 960 g
  2. temperatureis maintained below 25° C.
  3. temperaturewith cooling
  4. stirringThe mixture is stirred until the reaction
  5. custom(approximately one hour)
  6. customThe lower oxime layer is separated
  7. extractionthe aqueous layer is extracted with 2 liters of toluene
  8. extractionThe oxime layer and toluene extract
  9. washare washed twice with 1 liter of water

Sources & evidence

ORD record
ord-b567635ca7674190b2749d839fb987e9
Source dataset
uspto-grants-1989_09
Patent number
US04868327

Reaction notes

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