Reaction #1192

Reaction equation

2-ethylhexyl bromide

1,10-decanediol

KOH

→

10-(2-ethylhexyloxy)decanol

Yield 72.1%

Solvents

xylene

Conditions

Workup

1. 1
   OtherA 1-liter flask equipped with a stirrer
2. 2
   workup.DISTILLATIONdistilling off water
3. 3
   Otherformed
4. 4
   Temperaturethe resulting mixture was heated
5. 5
   OtherAfter completion of the reaction
6. 6
   Washwashed with water
7. 7
   workup.DISTILLATIONAfter the solvent was distilled off under reduced pressure
8. 8
   Otherthe resulting residue was purified by column chromatography on silica gel

Procedure

A 1-liter flask equipped with a stirrer and distiller was charged with 25 g (0.14 mol) of 1,10-decanediol, 8.09 g (0.14 mol) of KOH and 300 ml of xylene, and the resultant mixture was heated at 120° C. for 1 hour, thereby distilling off water formed. To this reaction mixture, were added 23.1 g (0.12 mol) of 2-ethylhexyl bromide, and the resulting mixture was heated and stirred for 15 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and washed with water. After the solvent was distilled off under reduced pressure, the resulting residue was purified by column chromatography on silica gel, thereby obtaining 24.8 g (yield: 72%) of 10-(2-ethylhexyloxy)decanol.

Source