m-Chloroperbenzoic acid → 4-Cyano-4'-glycidylbiphenyl

HRID 1982748Notes

Reaction equation

HRID 1982748 reaction equation
ClC1C=CC=[C:4]([C:8]([O:10]O)=O)[CH:3]=1.C(O[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)C=C>C(Cl)Cl>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([C:19]2[CH:18]=[CH:17][C:16]([CH2:3][CH:4]3[O:10][CH2:8]3)=[CH:21][CH:20]=2)=[CH:27][CH:26]=1)#[N:29]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 23419874-(4-Prop-2-enoxyphenyl)benzonitrile

Product 1

HCID 597905614-Cyano-4'-glycidylbiphenylYield 68.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. additionwas added in a few times to a solution
  2. customprepared
  3. filtrationThe deposited insoluble was filtered away
  4. additionwater was added to it for liquid-liquid separation
  5. washthe organic layer was washed with an aqueous saturated sodium hydrosulfite solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated away
  8. customthe residue was purified through silica gel column chromatography
  9. customfurther recrystallized from ethanol

Sources & evidence

ORD record
ord-183c3f584f464b6e83bcfeb80409b4b2
Source dataset
uspto-grants-2009_06
Patent number
US07541071B2

Reaction notes

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