m-Chloroperbenzoic acid → 3-Methyl-2-(methyloxy)-4-oxiran-2-ylbenzonitrile

HRID 1187004Notes

Reaction equation

HRID 1187004 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:11][CH3:12])[C:4]=1[CH3:13])=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl>[CH3:13][C:4]1[C:5]([O:11][CH3:12])=[C:6]([CH:9]=[CH:10][C:3]=1[CH:1]1[CH2:2][O:22]1)[C:7]#[N:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 666472914-Ethenyl-3-methyl-2-(methyloxy)benzonitrile

Product 1

HCID 772312543-Methyl-2-(methyloxy)-4-oxiran-2-ylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-ethenyl-3-methyl-2-(methyloxy)benzonitrile (3.90 g, 22.5 mmol) and m-CPBA (85%, 11.7 g, 67.6 mmol) in 300 mL of DCM was stirred at room temperature for 120 hours. The reaction mixture was cooled to 0° C. and was washed subsequently with saturated NaHCO3 (50 mL), saturated Na2SO3 (50 mL), 5% NaOH (50 mL×2) and brine (50 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography (PE:EtOAc=20:1) to afford 3-methyl-2-(methyloxy)-4-oxiran-2-ylbenzonitrile.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. washwas washed subsequently with saturated NaHCO3 (50 mL), saturated Na2SO3 (50 mL), 5% NaOH (50 mL×2) and brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (PE:EtOAc=20:1)

Sources & evidence

ORD record
ord-102946ce88f94a6daf9fa63db8b2245f
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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