Water → 8-Heptyloxy-octan-1-ol

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence