Epichlorohydrin → 4-(2-Oxiranylmethoxy)benzenecarbonitrile

HRID 411518Notes

Reaction equation

HRID 411518 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.C([O-])([O-])=O.[K+].[K+].[C:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)#[N:13]>CC#N>[O:5]1[CH2:4][CH:3]1[CH2:1][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]#[N:13])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

Product 1

HCID 27643014-(2-Oxiranylmethoxy)benzenecarbonitrileYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Epichlorohydrin (800 mL) and K2CO3 (414 g) were added to a stirred solution of p-cyanophenol (238 g) in 2.0 L MeCN and the reaction mixture was refluxed under inert atmosphere for 2 h. The hot solution was filtered and the filtrate concentrated to give a clear oil. This was crystallized from di-iso-propyl ether to give the sub-title compound in 75% yield.

Workup

  1. temperaturethe reaction mixture was refluxed under inert atmosphere for 2 h
  2. filtrationThe hot solution was filtered
  3. concentrationthe filtrate concentrated
  4. customto give a clear oil
  5. customThis was crystallized from di-iso-propyl ether

Sources & evidence

ORD record
ord-a9d546007ea3404495eb6b09a44c0443
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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