Hydrogen Cyanide → HCID 19079509, compound

Participants

Reaction Steps

23.7 g (0.338 mole) of methyl vinyl ketone were added over 5 minutes to a solution of 9.7 g (0.36 mole) of liquid hydrocyanic acid and 34 g of nitromethane whilst stirring, and thereafter 0.5 g of triethylamine was added slowly, first at -20° C. and then at -25° C. The reaction mixture was then kept at -20° C. for 1.5 hours. After acidifying the mixture with 1 g of phosphoric acid, 51.4 g (0.338 mole) of trimethylhydroquinone and 180 g of toluene were added, and 23.0 g (0.338 mole) of BF3 were then passed in over 1.5 hours at -10° C. After stirring for one hour at -5° C., the mixture was brought to room temperature and stirred for 5 hours. Working up by the method described in Example 1 gave pure 2-cyanochromane in 78% yield.

Provenance & Evidence