Hydrogen Bromide → 1-Octanol, 8-bromo-

HRID 2254915Notes

Reaction equation

HRID 2254915 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[BrH:11]>C1(C)C=CC=CC=1>[Br:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9]

Participants

4

Procedure

In a 6 m3 kettle, 235 kg of octane-1,8-diol were stirred under reflux with 3 m3 of toluene and 440 kg of HBr (48% strength) for 40 hours. The aqueous phase was then separated off. The toluene phase was thoroughly washed with 500 1 of water, then with 500 l of 10% strength sodium carbonate solution and then again with 500 1 of water. A sample was concentrated and was found to contain 92% of bromooctanol in addition to 1.9% of dibromooctane and 2.0% unconverted octanediol. After removal of the toluene by distillation in the reaction kettle and a Sambay distillation of the remaining residue, the yield was 254 kg (76%).

Workup

  1. customThe aqueous phase was then separated off
  2. washThe toluene phase was thoroughly washed with 500 1 of water
  3. concentrationA sample was concentrated
  4. additionin addition to 1.9% of dibromooctane and 2.0% unconverted octanediol
  5. customAfter removal of the toluene
  6. distillationby distillation in the reaction kettle
  7. distillationa Sambay distillation of the remaining residue

Sources & evidence

ORD record
ord-2dd3f3ab35d94dc6914d18ac935d2b39
Source dataset
uspto-grants-1993_08
Patent number
US05237113

Reaction notes

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