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

To a solution of 4-cyanophenol (6.55 g, 55.0 mmol) in anhydrous acetonitrile (50 mL) at ~0° C. under argon was added DBU (9.90 mL, 66.2 mmol). After the solution had cooled to ~0° C., 3-chloro-3-methyl-1-butyne (7.10 g, 69.2 mmol) was added followed by copper(II) acetylacetonate (87.4 mg, 033 mmol). After stirring at ~0° C. for 7 hours, the mixture was concentrated at reduced pressure. The residue was partitioned between 1N HCl (70 mL) and toluene (300 mL). The organic fraction was washed with 1N HCl (2×60 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 pale yellow oil. Distillation of the crude material (bulb to bulb) afforded the title compound as a colorless, low melting solid (9.56 g).

1. temperatureAfter the solution had cooled to ~0° C.
2. concentrationthe mixture was concentrated at reduced pressure
3. customThe residue was partitioned between 1N HCl (70 mL) and toluene (300 mL)
4. washThe organic fraction was washed with 1N HCl (2×60 mL), 1N NaOH (2×50 mL), 1N NaHCO3, and brine
5. dry with materialAfter drying (magnesium sulfate)
6. customthe solvent was removed at reduced pressure
7. customto give crude title compound as a pale yellow oil
8. distillationDistillation of the crude material (bulb to bulb)

ORD record

ord-815180bd9ba94fa588bc622220fbb291

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05463059