Guaiacol → (2-Methoxyphenoxy)acetonitrile

HRID 1824308Notes

Reaction equation

HRID 1824308 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15].Br[CH2:17][C:18]#[N:19]>CC(C)=O>[C:18]([CH2:17][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH3:7])#[N:19]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 11430Potassium CarbonateHCID 11534Bromoacetonitrile

Product 1

HCID 2736747(2-Methoxyphenoxy)acetonitrileYield 84.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Potassium carbonate (24 g) was added to a solution of of 2-methoxy phenol (18.94 g, 0.152 mol) in acetone (500 ml) at room temperature. A solution of bromoacetonitrile (17.43 g, 0.145 mol) in acetone (500 ml) was then added and the resulting suspension was heated at reflux for 10 h. The reaction vessel was then cooled and the solution was concentrated under reduced pressure and taken up into water (150 ml). Chloroform (250 ml) was added and the two layers separated. The organic phase was washed with brine (100 ml) and 10% aqueous NaOH (100 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure to give the product (19.91 g, 80%) as an oil. 1H NMR (CDCl3, 250 MHz) 7.0 (4H m), 4.8 (2H, s), 3.9 (3H, s).

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureat reflux for 10 h
  3. temperatureThe reaction vessel was then cooled
  4. concentrationthe solution was concentrated under reduced pressure
  5. additionChloroform (250 ml) was added
  6. customthe two layers separated
  7. washThe organic phase was washed with brine (100 ml) and 10% aqueous NaOH (100 ml)
  8. dry with materialThe organic phase was dried (MgSO4)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3df7fb7bb7b64d21a9d995366e78addf
Source dataset
uspto-grants-2006_05
Patent number
US07041684B2

Reaction notes

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