Potassium Carbonate → (S)-4-(Oxiran-2-ylmethoxy)benzonitrile

HRID 411132Notes

Reaction equation

HRID 411132 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C@@H:9]1[O:11][CH2:10]1)Cl.[C:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)#[N:13]>CC#N>[O:11]1[CH2:10][C@H:9]1[CH2:7][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 11430Potassium CarbonateHCID 130194-CyanophenolHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 6934187(S)-4-(Oxiran-2-ylmethoxy)benzonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (414 g) and (R)-(−)-epichlorohydrin (800 mL) were added to a stirred solution of p-cyanophenol (238 g) in 2.0 L MeCN and the reaction mixture was refluxed under an inert atmosphere for 2 h. The hot solution was filtered and the filtrate concentrated, giving a clear oil which was crystallised from di-iso-propyl ether giving the product in 90% yield.

Workup

  1. temperaturethe reaction mixture was refluxed under an inert atmosphere for 2 h
  2. filtrationThe hot solution was filtered
  3. concentrationthe filtrate concentrated
  4. customgiving a clear oil which
  5. customwas crystallised from di-iso-propyl ether giving the product in 90% yield

Sources & evidence

ORD record
ord-6dea3187b56942cd9a986f4c924cd51c
Source dataset
uspto-grants-2003_05
Patent number
US06559143B1

Reaction notes

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