Phenol → Phenyl cyanate

Temperature

0 °C

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.

1. customthermometer, and mechanical stirrer was placed
2. additionwas added dropwise at a rate not
3. customto rise above 15° C
4. filtrationfiltered through a glass frit
5. washThe filter cake was washed with pentane (2×400 mL)
6. concentrationthe combined filtrates were concentrated in vacuo
7. distillationdistilled

ORD record

ord-b1d5ba2518d7486eb0b48c4437aa1a19

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05162360