Hydrogen Bromide → 1-Octanol, 8-bromo-

HRID 722389Notes

Reaction equation

HRID 722389 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[BrH:11].O.C(=O)(O)[O-].[Na+]>C1CCCCC1>[Br:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 694201,8-OctanediolHCID 516892Sodium Bicarbonate

Product 1

HCID 1626071-Octanol, 8-bromo-

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

25 g of octane-1,8-diol was boiled in 250 ml of cyclohexane with 22.6 ml of 47% aqueous hydrobromic acid for six hours in a water separator. The reaction mixture was then poured onto saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was washed with saturated, aqueous sodium chloride solution, dried on sodium sulfate, filtered and concentrated by evaporation in a vacuum. Column chromatography on silica gel with a mixture that consists of hexane/ethyl acetate yielded 21.6 g of the title compound as a yellowish oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with saturated, aqueous sodium chloride solution
  3. customdried on sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-ca76bde0cb40461d8e95875824b57361
Source dataset
uspto-grants-2006_11
Patent number
US07138421B2

Reaction notes

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