1,12-Dibromododecane → 12-Bromo-1-dodecanol

HRID 987341Notes

Reaction equation

HRID 987341 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[Br:15]CCCCCCCCCCCCBr>Br>[Br:15][CH2:1][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 187661,12-DibromododecaneHCID 797581,12-Dodecanediol

Product 1

HCID 13789512-Bromo-1-dodecanol

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

1,12-Dodecanediol (50 g, 0.25 mol) in hydrogen bromide 48% (220 ml) was continuously extracted with petroleum ether (b.p. 80-100° C.) (300 ml) for 18 hours. The solvent was evaporated under reduced pressure and the crude oil obtained was filtered through a pad of silica gel. Elution with petroleum ether (b.p. 40-60° C.) gave a colourless fraction containing 1,12-dibromododecane. The silica gel was then eluted with acetone to give the title compound as a pale yellow oil after evaporation of the solvent. The title compound crystallised upon cooling and was recrystallised from petroleum ether (b.p. 40-60° C.).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude oil obtained
  3. filtrationwas filtered through a pad of silica gel
  4. washElution with petroleum ether (b.p. 40-60° C.)
  5. customgave a colourless fraction
  6. washThe silica gel was then eluted with acetone

Sources & evidence

ORD record
ord-b5dfeabbdc19488cbc2b002fe0a6b492
Source dataset
uspto-grants-2003_10
Patent number
US06630128B1

Reaction notes

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