Reaction #1193

Reaction equation

10-(2-ethylhexyloxy)decanol

epichlorohydrin

NaOH

→

10-(2-ethylhexyloxy)decyl glycidyl ether

Yield 82.6%

Solvents

hexane

Conditions

Workup

1. 1
   OtherA 200-ml flask equipped with a stirrer
2. 2
   Temperaturereflux tube
3. 3
   OtherAfter the resultant reaction mixture
4. 4
   Washwas washed with water
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
6. 6
   Otherthe resultant residue was purified by column chromatography on silica gel

Procedure

A 200-ml flask equipped with a stirrer, reflux tube and dropping funnel was charged with 24.8 g (87 mmol) of 10-(2-ethylhexyloxy)decanol, 17.7 g (0.191 mol) of epichlorohydrin, 1.4 g (4.4 mmol) of tetrabutylammonium bromide and 25 ml of hexane. While stirring the mixture at 40° C., 29.2 g (0.35 mol) of a 48% aqueous solution of NaOH were added dropwise over 3 hours. After completion of the dropping, the stirring was continued further for 2 hours at 40° C. After the resultant reaction mixture was washed with water, and the solvent was distilled off under reduced pressure, the resultant residue was purified by column chromatography on silica gel, thereby obtaining 24.6 g (yield: 82.6%) of 10-(2-ethylhexyloxy)decyl glycidyl ether.

Source