Benzaldehyde → (Z)-Benzaldehyde oxime

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence