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

Participants

Reaction Conditions

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 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).

Provenance & Evidence