Hydrogen Bromide → 1-Decanol, 10-bromo-

HRID 1092897Notes

Reaction equation

HRID 1092897 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[BrH:13]>C1CCCCC1.C(OCC)C>[Br:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11]

Participants

4

Reactant 2

HCID 260Hydrogen Bromide2×HCID 371531,10-Decanediol

Product 1

HCID 1045071-Decanol, 10-bromo-Yield 87%

Reagents, catalysts & solvents 1

HCID 21895417Cyclohexane diethyletherSolvent

Conditions

Temperature
30 °C

Procedure

87.8 g (0.50 mol) of 1,10-decanediol, 165.1 g of 48% strength hydrobromic acid and 2.5 l of high-boiling petroleum ether (b.p. 100-140° C.) were heated under reflux with vigorous stirring for 4 hours. A further 80.0 g of 48 strength hydrobromic acid were added, and the mixture was boiled for 5 hours. After cooling to 30° C., the phases were separated. The organic phase was washed first with a solution of 100 g of Na2CO3 in 500 ml of water and then with 2×500 ml of water. Removal of the solvent was followed by chromatography on 700 g of silica gel. The byproduct 1,10-dibromodecane was eluted with cyclohexane/diethyl ether (20:1). Chromatography with cyclohexane/diethyl ether (2:1) afforded 103.9 g (0.44 mol, 87%) of 10-bromo-1-decanol.

Workup

  1. temperatureunder reflux
  2. waitthe mixture was boiled for 5 hours
  3. customthe phases were separated
  4. washThe organic phase was washed first with a solution of 100 g of Na2CO3 in 500 ml of water
  5. customRemoval of the solvent
  6. washThe byproduct 1,10-dibromodecane was eluted with cyclohexane/diethyl ether (20:1)

Sources & evidence

ORD record
ord-784af2bb7e3b402e8a89becb53e6f7b4
Source dataset
uspto-grants-2012_03
Patent number
US08129552B2

Reaction notes

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