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

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-cyanophenol (655 g, 5.50 mol) in acetonitrile (10 L) at 0° C. under nitrogen was added cuprous chloride (495 mg, 5 mmol, 0.001 eq., 0.1 mol %). DBU (970 mL 6.51 mol) was added slowly while maintaining the temperature at <5° C. 3-Chloro-3-methyl-1-butyne (570 mL, 5 mole) was added. After stirring for 4 hours at 0° C., the mixture was concentrated at reduced pressure and the residue was partitioned between ethyl acetate (5 L) and 1N HCl (2 L). The organic fraction was washed with 1N NaOH (2×1 L), water (1 L), and brine (1 L). After drying (magnesium sulfate), the solvent was removed at reduced pressure to afford the title compound as a yellow oil (930 g) which was used without further purification.

Provenance & Evidence