Sodium Chloride → 8-Heptyloxy-octanal

Participants

Reaction Conditions

Reaction Steps

8-Heptyloxy-octan-1-ol (No. 6804253; 193.8 mg, 0.793 mmol) was dissolved in toluene (1.36 mL), and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO; 1.2 mg, 0.00768 mmol) and an aqueous solution (1.33 mL) of 5% sodium bicarbonate were added in order. The mixture was cooled to 0° C. While maintaining the temperature at 0° C., an aqueous solution (492 μL) of 12% sodium chloride was added. The mixture was stirred at 0° C. for 2.0 minutes and at room temperature for 2.0 hours. TEMPO (2.4 mg, 0.0154 mmol) and an aqueous solution (49.2 μL) of 12% sodium chloride were added further. The mixture was stirred at room temperature for 1 hour. Ethyl acetate and water were added, and the mixture was extracted. The organic layer was washed with water and a saturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off. The resulting residue was then purified with SP1 (SiO2 cartridge, 50% ethyl acetate/n-hexane, Rf=0.3) to obtain the target compound, 8-heptyloxy-octanal (ESI (LC/MS positive mode) m/z 243 (M+H); Rt 2.35 min.; 178.0 mg, 93% yield).

Provenance & Evidence