Borane → 11-Bromo-1-undecanol

HRID 648300Notes

Reaction equation

HRID 648300 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](O)=[O:13].B>O1CCCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 6331BoraneHCID 1781211-Bromoundecanoic acid

Product 1

HCID 7416311-Bromo-1-undecanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5 g. of 11-bromoundecanoic acid and 20 ml. of tetrahydrofuran is stirred at 0° C. while 16 ml. of 1 M borane in tetrahydrofuran is added during 15 minutes. The mixture is stirred 18 hours at ambient temperature, poured into ice-water, and extracted with ether. The dried extract is evaporated and the residual oil crystallized from hexane to yield 11-bromoundecanol as a white solid.

Workup

  1. extractionextracted with ether
  2. extractionThe dried extract
  3. customis evaporated
  4. customthe residual oil crystallized from hexane

Sources & evidence

ORD record
ord-7c8edd0079294f1186b58be50c255a3c
Source dataset
uspto-grants-1983_10
Patent number
US04411903

Reaction notes

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