Reaction #577214

Reaction equation

m-chlorobenzoic acid

4-allyloxy-4′-cyanobiphenyl

→

4-cyano-4′-glycidylbiphenyl

Yield 68.4%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Otherobtained
2. 2
   OtherInsoluble matters thus deposited were removed by filtration, and water
3. 3
   workup.ADDITIONwas added
4. 4
   OtherAfter separating the mixture
5. 5
   Washthe organic layer was washed with a saturated aqueous solution of sodium hydrosulfite
6. 6
   Dryingdried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off
8. 8
   Otherto obtain a residue, which
9. 9
   Otherwas purified by silica gel column chromatography
10. 10
    Othersubjected to recrystallization from ethanol

Procedure

20 g of m-chlorobenzoic acid was added to a reaction mixture obtained by dissolving 19 g of 4-allyloxy-4′-cyanobiphenyl in 150 mL of methylene chloride as divided into several times, and the mixture was stirred at room temperature for 24 hours. Insoluble matters thus deposited were removed by filtration, and water was added thereto. After separating the mixture, the organic layer was washed with a saturated aqueous solution of sodium hydrosulfite and then dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain a residue, which was purified by silica gel column chromatography and then subjected to recrystallization from ethanol to obtain 13 g of 4-cyano-4′-glycidylbiphenyl.

Source