4-Cyanophenol → 4-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile
Reaction equation
F[C:2](F)(F)[C:3]([O:5][C:6]([CH3:10])([CH3:9])[C:7]#[CH:8])=O.[C:13]([C:15]1[CH:20]=CC(O)=[CH:17][CH:16]=1)#[N:14]>O>[CH3:9][C:6]([O:5][C:3]1[CH:17]=[CH:16][C:15]([C:13]#[N:14])=[CH:20][CH:2]=1)([CH3:10])[C:7]#[CH:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The 1,1-dimethyl-2-propynyl trifluoroacetate solution, maintained at 0° C., was added to the 4-cyanophenol solution over a 35 minute period while keeping the temperature at ~0° C. The resulting mixture was stirred at ~0° C. (ice bath). After stirring for 90 minutes, water (10 mL) was added and the resulting mixture was concentrated at reduced pressure. The residue was partitioned between water (50 mL) and toluene (300 mL). The organic fraction was washed with 1N HCl (3×50 mL), 1N NaOH (2×50 mL), 1N NaHCO3, and brine. After drying (magnesium sulfate), the solvent was removed at reduced pressure to give crude title compound as a yellow oil. Distillation of the crude material (bulb to bulb) afforded the title compound as a colorless, low melting solid (8.93 g).
Workup
- customat ~0° C
- stirringAfter stirring for 90 minutes
- concentrationthe resulting mixture was concentrated at reduced pressure
- customThe residue was partitioned between water (50 mL) and toluene (300 mL)
- washThe organic fraction was washed with 1N HCl (3×50 mL), 1N NaOH (2×50 mL), 1N NaHCO3, and brine
- dry with materialAfter drying (magnesium sulfate)
- customthe solvent was removed at reduced pressure
- customto give crude title compound as a yellow oil
- distillationDistillation of the crude material (bulb to bulb)
Sources & evidence
- ORD record
- ord-627fbe6701bd499a8d4d5943c117a551
- Source dataset
- uspto-grants-1995_10
- Patent number
- US05463059
Reaction notes
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