Hydrogen Bromide → 1-Octanol, 8-bromo-
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
Reagents, catalysts & solvents 1
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
- customThe aqueous phase was then separated off
- washThe toluene phase was thoroughly washed with 500 1 of water
- concentrationA sample was concentrated
- additionin addition to 1.9% of dibromooctane and 2.0% unconverted octanediol
- customAfter removal of the toluene
- distillationby distillation in the reaction kettle
- distillationa Sambay distillation of the remaining residue
Sources & evidence
- ORD record
- ord-2dd3f3ab35d94dc6914d18ac935d2b39
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05237113
Reaction notes
Loading…