Sodium Chloride → 8-Heptyloxy-octanal

Temperature

0 °C

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).

1. temperatureWhile maintaining the temperature at 0° C.
2. stirringThe mixture was stirred at room temperature for 1 hour
3. extractionthe mixture was extracted
4. washThe organic layer was washed with water
5. dry with materiala saturated brine, dried over anhydrous sodium sulfate
6. filtrationfiltered
7. distillationThe solvent was distilled off
8. customThe resulting residue was then purified with SP1 (SiO2 cartridge, 50% ethyl acetate/n-hexane, Rf=0.3)

ORD record

ord-bc61b3e479d14005b0b7a8b53974dae1

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266853B2