Epichlorohydrin → 4-(2-Oxiranylmethoxy)benzenecarbonitrile

HRID 2180007Notes

Reaction equation

HRID 2180007 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]>C(#N)C>[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 of acetonitrile. The reaction mixture was brought to reflux under an inert atmosphere for 2 h before being filtered whilst still hot. The resulting filtrate was concentrated to give a clear oil. This was crystallized from di-iso-propyl ether to give the sub-title compound in a 75% yield.

Workup

  1. temperatureto reflux under an inert atmosphere for 2 h
  2. filtrationbefore being filtered whilst still hot
  3. concentrationThe resulting filtrate was concentrated
  4. customto give a clear oil
  5. customThis was crystallized from di-iso-propyl ether

Sources & evidence

ORD record
ord-42a3410c6d7b477595fce9aa6e40c2cd
Source dataset
uspto-grants-2005_05
Patent number
US06887881B1

Reaction notes

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