18-Pentatriacontanone → 18-Pentatriacontanol

Participants

Reaction Steps

18-Hydroxypentatriacontane (2-1) was prepared as follows and used without further purification. In a dry flask charged with argon was prepared a solution of lithium aluminum hydride (0.75 g, (19.8 mmol)) in freshly distilled tetrahydrofuran (400 mL). To this solution was added stearone (5.0 g, (9.9 mmol)). The reaction mixture was slowly brought to reflux (and allowed to stir at reflux overnight). After cooling to room temperature, the remaining lithium aluminum hydride was quenched by the dropwise addition of water (0.76 mL), followed by 15% NaOH (0.76 mL), and water again (2.2 mL). The reaction mixture was allowed to stir for 1 hour. The solvent was evaporated, and the resulting solids were triturated with hot toluene (300 mL). The toluene was evaporated to yield the desired alcohol (4.9 g. 97% yield) 1H NMR (300 MHz, CDCl3, TMS=0), δ3.58 (m, 1H), 1.38 (m, 4H), 1.25 (bs, 60H), 0.88 (t, 6H, J=6.5).

Provenance & Evidence