m-Chloroperbenzoic acid → 4-[2-(Oxiran-2-yl)ethoxy]benzonitrile

HRID 1743728Notes

Reaction equation

HRID 1743728 reaction equation
[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl>[O:22]1[CH2:4][CH:3]1[CH2:2][CH2:1][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]#[N:11])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 139723854-[(But-3-en-1-yl)oxy]benzonitrile

Product 1

HCID 222353954-[2-(Oxiran-2-yl)ethoxy]benzonitrileYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Butenyloxy)benzonitrile (37 g, 0.21 mol; from step (c) above) was mixed with mCPBA (61.6 g, 0.25 mol) and DCM (700 mL) and stirred at r.t for 4 h. The reaction mixture was filtered and 2 mL of DMSO added to destroy the excess mCPBA. The mixture was washed with NaHCO3, then separated, dried and evaporated to give 38.7 g (97%) of the sub-title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. addition2 mL of DMSO added
  3. customto destroy the excess mCPBA
  4. washThe mixture was washed with NaHCO3
  5. customseparated
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-28f09e5cf38f454287d3c786a17a9551
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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