Sodium Cyanide → HCID 13882115, compound

Participants

Reaction Steps

To a 100 milliliter flask provided with a magnetic stirring bar and a drying tube were charged 0.5 gram of 2-[4-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionaldehyde, 0.5 gram of sodium cyanide, 0.12 gram of tetrabutyl ammonium hydrogen sulfate, 30 milliliters of methylene chloride and 0.2 milliliter of ethyl chlorocarbonate. After stirring overnight at room temperature, TLC analysis indicated the presence of a considerable amount of unreacted starting material so an additional 0.5 gram of sodium cyanide and 0.2 milliliter of ethyl chlorocarbonate were added and stirring was continued for 2.5 hours after which time an additional 0.2 milliliter of ethyl chlorocarbonate was added. After stirring an additional hour TLC indicated presence of some starting material so 1.0 gram of potassium cyanide and 0.1 gram of 18-crown-6 were added. After stirring at room temperature, an additional 1.5 hours, the reaction mixture was transferred to a separatory funnel, diluted with 150 milliliters of diethyl ether and washed with 4×50 milliliter portions of water. The organic layer was dried and evaporated affording about 1.0 gram of a brown, viscous residue. The residue was dissolved in methylene chloride and eluted over silica gel using methylene chloride as the eluent. The first four 50 milliliter fractions were combined and evaporated affording about 0.6 gram of colorless, gummy material confirmed by PMR analysis as the desired product.

Provenance & Evidence