Reaction #1328416

Reaction equation

2-allyl-6-chlorobenzaldehyde

sodium bicarbonate

hydroxylamine hydrochloride

→

2-Allyl-6-chlorobenzaldehyde oxime

Solvents

methanol

water

Conditions

Workup

1. 1
   OtherThe methanol was subsequently removed under reduced pressure
2. 2
   workup.STIRRINGthe residue was stirred into 300 ml of water
3. 3
   ExtractionThe aqueous phase was extracted with diethyl ether
4. 4
   Washthe combined organic phases were washed with saturated ammonium chloride solution
5. 5
   Otherdried
6. 6
   Otherthe solvent was removed

Procedure

5.58 g of sodium bicarbonate were added to a solution of 4.62 g of hydroxylamine hydrochloride in 50 ml of water, and the mixture was cooled to 0° C. A solution of 9.7 g (44.32 mmol) of 2-allyl-6-chlorobenzaldehyde in 50 ml of methanol was then added dropwise, and the mixture was stirred at room temperature overnight. The methanol was subsequently removed under reduced pressure and the residue was stirred into 300 ml of water. The aqueous phase was extracted with diethyl ether and the combined organic phases were washed with saturated ammonium chloride solution and dried, and the solvent was removed. This gave 8.7 g (quantitative) of 2-allyl-6-chlorobenzaldehyde oxime in the form of a viscous oil.

Source