Reaction #1328417

Reaction equation

sodium hypochlorite

2-allyl-6-chlorobenzaldehyde oxime

sodium acetate

→

8-Chloro-3a,4-dihydro-3H-indeno[1,2-c]isoxazole

Solvents

methylene chloride

Conditions

Workup

1. 1
   Otherthe organic phase was separated off
2. 2
   Extractionthe aqueous phase was extracted with methylene chloride
3. 3
   Washthe combined organic phases were washed with saturated ammonium chloride solution
4. 4
   OtherThe organic phase was dried
5. 5
   Otherthe solvent was removed

Procedure

At room temperature, 37.0 ml of a sodium hypochlorite solution (12.5% of active chlorine) were added dropwise to a solution of 8.4 g (42.9 mmol) of 2-allyl-6-chlorobenzaldehyde oxime in 100 ml of methylene chloride, and a spatula tip of sodium acetate was added. The mixture was stirred at room temperature for 2 hours, the organic phase was separated off, the aqueous phase was extracted with methylene chloride and the combined organic phases were washed with saturated ammonium chloride solution. The organic phase was dried and the solvent was removed. This gave 7.0 g (94%) of 8-chloro-3a,4-dihydro-3H-indeno-[1,2-c]isoxazole in the form of a viscous oil.

Source