11-Bromoundecanoic acid → 11-Bromo-1-undecanol

Sodium Borohydride (28.8 g, 0.76 mole) was dissolved in diglyme (700 ml) and THF (300 ml) and the solution cooled to 20° (dissolution of the NaBH4 is slightly exothermic). BF3OEt2 (145 g, 1.02 mole) was then added dropwise, with external cooling, at such a rate to keep the temperature of the mixture below 15°. After the addition was complete the mixture was stirred for 0.5 hour at 10°. This reducing agent was then added slowly to a solution of 11-bromoundecanoic acid (200 g, 0.76 mole) in THF (400 ml) keeping the temperature below 20°. After the addition was complete, the reaction was stirred at room temperature for 1.5 hours then quenched by pouring onto water (3 L) and concentrated HCl (100 ml). The quenched mixture was stirred for 0.5 hour at room temperature then cooled to 5°. The crystalline product was filtered off, washed with water (3×1 L) and dried under vacuum to give 11-bromoundecanol (189.2 g, 99.2%).

1. additionBF3OEt2 (145 g, 1.02 mole) was then added dropwise, with external cooling
2. customthe temperature of the mixture below 15°
3. additionAfter the addition
4. customthe temperature below 20°
5. additionAfter the addition
6. stirringthe reaction was stirred at room temperature for 1.5 hours
7. customthen quenched
8. additionby pouring onto water (3 L) and concentrated HCl (100 ml)
9. stirringThe quenched mixture was stirred for 0.5 hour at room temperature
10. temperaturethen cooled to 5°
11. filtrationThe crystalline product was filtered off
12. washwashed with water (3×1 L)
13. customdried under vacuum

ORD record

ord-72560b12457b41f08e11a500b274e647

Source dataset

uspto-grants-1995_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05441731