Triethylamine → HCID 15405387, compound

To a solution of 2.142 g (15.96 mmol) of 4-(2-propenyl)phenol (prepared as in Example 1) in 15 mL of methylene chloride was added 2.351 g (22.19 mmol) of cyanogen bromide (Aldrich). The mixture was cooled in an ice-salt bath and 3 mL (22 mmol) of triethylamine was added dropwise with stirring. The mixture was stirred for an additional 15 minutes. The solvent was removed under vacuum and the mixture was transferred to a separatory funnel with 25 mL of water and 75 mL of petroleum ether (30-60° C. boiling range). The aqueous and organic layers were separated. The organic layer was washed with three 50 mL portions 6 N hydrochloric and one 50 mL portion of saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under vacuum to yield 1.668 g (66%) of crude 1-cyanato-4-(2-propenyl)benzene. The product was distilled to yield 1.307 g (51%) of 1-cyanato-4-(2-propenyl)benzene. The structure of the product was verified by IR and NMR spectroscopy. The product can be further purified by passing the product through a silica gel column using 1% toluene in petroleum ether as the solvent system.

1. temperatureThe mixture was cooled in an ice-salt bath
2. stirringThe mixture was stirred for an additional 15 minutes
3. customThe solvent was removed under vacuum
4. customthe mixture was transferred to a separatory funnel with 25 mL of water and 75 mL of petroleum ether (30-60° C. boiling range)
5. customThe aqueous and organic layers were separated
6. washThe organic layer was washed with three 50 mL portions 6 N hydrochloric
7. dry with materialone 50 mL portion of saturated sodium bicarbonate, dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. customThe solvent was removed under vacuum

ORD record

ord-efaf547bfc2f47fb8793d8467ac25d52

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06217943B1