Reaction #1180079

Reaction equation

1,10-decanediol

hydrobromic acid

hydrobromic acid

→

10-bromo-1-decanol

Yield 87.0%

Solvents

—

petroleum ether

cyclohexane diethyl ether

Conditions

Workup

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

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.

Source