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

Participants

Reaction Steps

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 anhydrous acetonitrile (24 mL) at 0° C. under argon was added DBU (5.0 mL, 33.43 mmol). After the solution had cooled to ~0° C., copper(II) acetylacetonate (66.4 mg, 0.254 mmol) was added. After stirring at ~0° C. for 72 hours, the mixture was concentrated at reduced pressure. The residue was partitioned between 1N HCl (40 mL) and toluene (200 mL). The organic fraction was washed with 1N HCl (2×40 mL), 1N NaOH (2×40 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 (4.59 g).

Provenance & Evidence