Water → 8-Heptyloxy-octan-1-ol

Temperature

50 °C

At room temperature, a commercially available reagent of octane-1,8-diol (351.2 mg, 2.40 mmol) was dissolved in DMF (3.0 mL), and sodium hydride (60 wt %, 105.7 mg, 2.64 mmol) was added. The mixture was then warmed to 50° C., stirred for 10 hours while maintaining the temperature at 50° C., and cooled to room temperature. 1-Bromo-heptane (430.2 mg, 2.40 mmol) in DMF (1.5 mL) was then added, and the mixture was stirred at room temperature for 48 hours. The progress of reaction was stopped by adding water. Ethyl acetate was 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=0.8) to obtain 8-heptyloxy-octan-1-ol (No. 6804253; 193.8 mg, 33% yield).

1. temperaturewhile maintaining the temperature at 50° C.
2. temperaturecooled to room temperature
3. stirringthe mixture was stirred at room temperature for 48 hours
4. customThe progress of reaction
5. extractionthe mixture was extracted
6. washThe organic layer was washed with water
7. dry with materiala saturated brine, dried over anhydrous sodium sulfate
8. filtrationfiltered
9. distillationThe solvent was distilled off
10. customThe resulting residue was then purified with SP1 (SiO2 cartridge, 50% ethyl acetate/n-hexane, Rf=0.8)

ORD record

ord-508e18f013fc4ec0a09a700cc397217c

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266853B2