Acrylonitrile → 3-(4-Methoxyphenoxy)propanenitrile

HRID 346043Notes

Reaction equation

HRID 346043 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[OH-].[K+].[C:12](#[N:15])[CH:13]=[CH2:14]>C(O)(C)(C)C.CCOCC>[C:12]([CH2:13][CH2:14][O:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)#[N:15]

Participants

6

Reactant 3

HCID 7855AcrylonitrileHCID 90154-MethoxyphenolHCID 14797Potassium Hydroxide

Product 1

HCID 1142473-(4-Methoxyphenoxy)propanenitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
75 °C

Procedure

4-Methoxyphenol (248 g), KOH (5.6 g) and acrylonitrile (397 ml) were dissolved in 1 liter of t-butanol and heated with stirring at 75° C. for 5 hours. The mixture was then cooled to room temperature and stripped in vacuo to solid residue, which was repulped in ether and insolubles recovered by filtration. The latter were taken up in 2 liters of ethyl acetate, washed in sequence with 1 liter each of H2O, saturated NaHCO3 and saturated NaCl, dried over MgSO4 and restripped to yield purified title product, 199.4 g, m.p. 62°-64° C.

Workup

  1. temperatureheated
  2. temperatureThe mixture was then cooled to room temperature
  3. filtrationinsolubles recovered by filtration
  4. washwashed in sequence with 1 liter each of H2O, saturated NaHCO3 and saturated NaCl
  5. dry with materialdried over MgSO4
  6. customto yield
  7. custompurified title product, 199.4 g, m.p. 62°-64° C.

Sources & evidence

ORD record
ord-20612c9a3dc44f2ba0c18f43a794071b
Source dataset
uspto-grants-1991_10
Patent number
US05059609

Reaction notes

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