Acrylonitrile → 3-(4-Methoxyphenoxy)propanenitrile
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
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
4-Methoxyphenol (248 g), KOH (5.6 g) and acrylo-nitrile (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
- temperatureheated
- temperatureThe mixture was then cooled to room temperature
- filtrationinsolubles recovered by filtration
- washwashed in sequence with 1 liter each of H2O, saturated NaHCO3 and saturated NaCl
- customdried over MgSo4
- customto yield
- custompurified title product, 199.4 g, m.p. 62-64° C.
Sources & evidence
- ORD record
- ord-ebb828bdced2423db50b0cb15ce2fc20
- Source dataset
- uspto-grants-1999_12
- Patent number
- US05998451
Reaction notes
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