4-Cyanophenol → 4-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile

HRID 2211231Notes

Reaction equation

HRID 2211231 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]>>[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

3

Reactant 2

HCID 130194-CyanophenolHCID 11830027Acetic acid, trifluoro-, 1,1-dimethyl-2-propynyl ester

Product 1

HCID 27790724-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile

Procedure

The 1,1-dimethyl-2-propynyl trifluoroacetate solution, maintained at 0° C., was added to the 4-cyanophenol solution over a 40 minute period while keeping the temperature at ~0° C. The resulting mixture was stirred at ~0° C. (ice bath). After stirring for 5 hours, the 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 very pale yellow oil. Distillation of the crude material (bulb to bulb) afforded the title compound as a colorless, low melting solid (8.04 g).

Workup

  1. customat ~0° C
  2. stirringAfter stirring for 5 hours
  3. concentrationthe mixture was concentrated at reduced pressure
  4. customThe residue was partitioned between water (50 mL) and toluene (300 mL)
  5. washThe organic fraction was washed with 1N HCl (3×50 mL), 1N NaOH (2×50 mL), 1N NaHCO3, and brine
  6. dry with materialAfter drying (magnesium sulfate)
  7. customthe solvent was removed at reduced pressure
  8. customto give crude title compound as a very pale yellow oil
  9. distillationDistillation of the crude material (bulb to bulb)

Sources & evidence

ORD record
ord-2972fa5d409f4ff19e89e80f4b5b124e
Source dataset
uspto-grants-1995_10
Patent number
US05463059

Reaction notes

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