Methyl 11-bromoundecanoate → 11-Bromo-1-undecanol

Participants

Reaction Steps

Sodium Borohydride (16.32 g, 0.43 mole) was dissolved in diglyme (350 ml). To this was added a solution of aluminium trichloride (19.2 g, 0.14 mole) in diglyme (250 ml) maintaining the temperature below 20°. After the addition was complete, the mixture was stirred for 0.5 hour at room temperature. The reducing agent was then added dropwise to a solution of methyl 11-bromoundecanoate* (120 g, 0.43 mole) in diglyme (200 ml) maintaining the temperature at 10°. After the addition was complete the reaction was stirred at 20° for 3 hours and then quenched by pouring onto water (2 L) and concentrated HCl (100 ml). The quenched mixture was stirred for 1 hour then cooled to 15°. The product was filtered off, washed with water (2×500 ml) and dried under vacuum to give 11-bromoundecanol (106.8 g, 98.9%).

Provenance & Evidence