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

HRID 1596472Notes

Reaction equation

HRID 1596472 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[C:12]([C:14]1[CH:24]=[CH:23][C:17]([O:18][CH2:19][CH2:20][CH:21]=[CH2:22])=[CH:16][CH:15]=1)#[N:13]>C(Cl)Cl>[O:9]1[CH2:22][CH:21]1[CH2:20][CH2:19][O:18][C:17]1[CH:23]=[CH:24][C:14]([C:12]#[N:13])=[CH:15][CH:16]=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]benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (15.9 g; 65 mmol) was added to a stirred solution of 4-(4′-cyanophenoxy)but-1-ene (7.5 g; 56 mmol; prepared according to the method described in J. Chem. Soc. Perkin Trans. 1, 9 (1992) 1145-1148) in CH2Cl2 (175 mL) and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was washed with NaHCO3 (aq.) and the organic layer separated, dried and concentrated to give the sub-title compound (7.23 g; 38 mmol).

Workup

  1. customprepared
  2. washThe reaction mixture was washed with NaHCO3 (aq.)
  3. customthe organic layer separated
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1a0be52031c846eb9902f8f9cc30235e
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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