1-Octanol → Octanal

Participants

Reaction Conditions

Reaction Steps

To a solution of N-chlorosuccinimide (0.1 g, 0.8 mmol) in toluene (2 mL) was added flurous sulfide 1 (0.4 g, 1 mmol) at 0° C. resulting in the immediate formation of a white cloudy precipitate. The reaction mixture was cooled to −25° C., and a solution of octanol (0.07 g, 0.5 mmol) in toluene (2 mL) was added. After stirring at −25° C. for 2 hours, a solution of Et3N (0.08 g, 0.8 mmol) was added. The cold bath was removed after 5 minutes, and the reaction mixture washed with saturated aqueous NH4Cl, then water. The organic layer was extracted continuously with FC72 solvent (15 mL) in a cooled continuous extractor for a period of 4 hours. Concentration of the toluene layer and chromatography on silica gel (eluent: EtOAc/hexanes 3:1) yielded octanal (0.06 g, 88%). The FC72 layer was carefully concentrated under aspirator vacuum to give recovered fluorous sulfide 1 (0.3 g, 75%).

Provenance & Evidence