Phenol → Phenyl cyanate

Participants

Reaction Conditions

Reaction Steps

Into a 2-L three neck flask equipped with a drop-in funnel, thermometer, and mechanical stirrer was placed phenol (84.3 g, 0.896 mol), cyanogen bromide (100.0 g, 0.944 mol), anhydrous ether (450 mL), and pentane (450 mL). The resulting solution was cooled (0° C.), and while stirring vigorously triethylamine 131.6 mL, 0.944 mol) was added dropwise at a rate not allowing the temperature to rise above 15° C. The resulting slurry was stirred vigorously (1 hour, 0° C.), then filtered through a glass frit. The filter cake was washed with pentane (2×400 mL), and the combined filtrates were concentrated in vacuo, then distilled to yield 94.1 g (88.2%) of phenyl cyanate as a clear liquid, b.p. 76°-79° C., 15 mm.

Provenance & Evidence