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

HRID 1756485Notes

Reaction equation

HRID 1756485 reaction equation
[BH4-].[Na+].[Cl-].[Cl-].[Cl-].[Al+3].[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](OC)=[O:19]>COCCOCCOC>[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19]

Participants

5

Reactant 3

HCID 223913Methyl 11-bromoundecanoateHCID 4311764Sodium borohydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 7416311-Bromo-1-undecanolYield 98.9%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent3×

Procedure

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%).

Workup

  1. temperaturemaintaining the temperature below 20°
  2. additionAfter the addition
  3. temperaturemaintaining the temperature at 10°
  4. additionAfter the addition
  5. stirringwas stirred at 20° for 3 hours
  6. customquenched
  7. additionby pouring onto water (2 L) and concentrated HCl (100 ml)
  8. stirringThe quenched mixture was stirred for 1 hour
  9. temperaturethen cooled to 15°
  10. filtrationThe product was filtered off
  11. washwashed with water (2×500 ml)
  12. customdried under vacuum

Sources & evidence

ORD record
ord-0bdadb8cbfcd45bd85beadb963c20cf5
Source dataset
uspto-grants-1995_08
Patent number
US05441731

Reaction notes

Loading…