4-Cyanophenol → 4-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C(=O)(O[C:14]([CH3:18])([CH3:17])[C:15]#[CH:16])OC.C1CCN2C(=NCCC2)CC1>C(#N)C.[Cu]>[CH3:17][C:14]([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)([CH3:18])[C:15]#[CH:16]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-cyanophenol (3.0 g, 25.18 mmol) and methyl 1,1-dimethyl-2-propynyl carbonate (3.93 g, 27.64 mmol) in acetonitrile (24 mL) at 0° C. under argon was added DBU (5.0 mL, 33.43 mmol). To the resulting solution at 0° C. was added cuprous chloride (7.47 mg, 0.003 eq., 0.3 mol %) and copper bronze (83 mg). After stirring at 0° C. for 23 hours, the reaction mixture was filtered and the filtrate was diluted with toluene (~400 mL). The resulting solution was washed with 1N HCl (×2), 1N NaOH (×2), and brine. After drying (magnesium sulfate), the solvent was removed at reduced pressure to give crude title compound as a pale yellow oil (4.18 g). Distillation of the crude material (bulb-to-bulb) afforded the title compound as a colorless, low melting (mp 28°-29° C.) solid (4.02 g).
Workup
- filtrationthe reaction mixture was filtered
- additionthe filtrate was diluted with toluene (~400 mL)
- washThe resulting solution was washed with 1N HCl (×2), 1N NaOH (×2), and brine
- dry with materialAfter drying (magnesium sulfate)
- customthe solvent was removed at reduced pressure
- customto give crude title compound as a pale yellow oil (4.18 g)
- distillationDistillation of the crude material (bulb-to-bulb)
Sources & evidence
- ORD record
- ord-95f3292b1ed448afbf399b67b0efaa6c
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05536833
Reaction notes
Loading…