Triphenylphosphine → HCID 178447869, compound

Participants

Reaction Steps

While 4-(trans-4-n-propylcyclohexyl)benzaldehyde (25 g, 0.11 mol), triphenylphosphine (31 g, 0.12 mol) and diethylene glycol dimethyl ether (25 ml) were heated at 160° C. in nitrogen gas current with stirring, a solution of sodium chlorodifluoroacetate (25 g, 0.16 mol) in diethylene glycol dimethyl ether (70 ml) at 70° C. was dropwise added to the above solution over 2 hours, followed by cooling the resulting solution, filtering it by suction, concentrating the filtrate under reduced pressure, distilling the concentrate under reduced pressure (150° C., 3 mmHg), dissolving the distillate in toluene (100 ml), washing the toluene solution three times with 6N-hydrochloric acid (100 ml) and further with water till the washing water became neutral, drying the toluene solution with anhydrous sodium sulfate, separating the drying agent, distilling off toluene, recrystallizing the residue from a mixed solvent of heptane with ethanol (1:5), dissolving the resulting crystals in heptane, purifying the solution according to silica gel column chromatography, again distilling the resulting solution under reduced pressure, three times recrystallizing the residue from a mixed solvent of heptane with ethanol (1:5) and finally drying the resulting crystals to obtain the objective product (10 g, 0.04 mol).

Provenance & Evidence