Reaction #2069930

Reaction equation

m-chloroperbenzoic acid

4-allyloxy-4′-cyanobiphenyl

→

4-cyano-4′-glycidylbiphenyl

Yield 68.4%

Solvents

methylene chloride

Conditions

Workup

1. 1
   workup.ADDITIONwas added in a few times to a solution
2. 2
   Otherprepared
3. 3
   FiltrationThe deposited insoluble was filtered away
4. 4
   workup.ADDITIONwater was added to it for liquid-liquid separation
5. 5
   Washthe organic layer was washed with an aqueous saturated sodium hydrosulfite solution
6. 6
   Dryingdried with anhydrous magnesium sulfate
7. 7
   OtherThe solvent was evaporated away
8. 8
   Otherthe residue was purified through silica gel column chromatography
9. 9
   Otherfurther recrystallized from ethanol

Procedure

20 g of m-chloroperbenzoic acid divided into portions was added in a few times to a solution prepared by dissolving 19 g of 4-allyloxy-4′-cyanobiphenyl in 150 ml of methylene chloride, and stirred at room temperature for 24 hours. The deposited insoluble was filtered away, water was added to it for liquid-liquid separation, and the organic layer was washed with an aqueous saturated sodium hydrosulfite solution and then dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the residue was purified through silica gel column chromatography and further recrystallized from ethanol to obtain 13 g of 4-cyano-4′-glycidylbiphenyl.

Source