Reaction #167595

Reaction equation

Epichlorohydrin

potassium tert-butoxide

epichlorohydrin

2-ethylhexanol

1-chloro-3-(2-ethyl-hexyloxy)-propan-2-ol

1-chloro-3-(2-ethyl-hexyloxy)-propan-2-ol

→

2-ethylhexyl glycidyl ether

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   OtherTo a flame dried
2. 2
   Other500 mL round bottomed flask equipped with an addition funnel
3. 3
   workup.DISTILLATIONis distilled under 0.2 mm Hg
4. 4
   workup.STIRRINGstirred at room temperature under an argon atmosphere
5. 5
   workup.STIRRINGthe suspension is stirred at room temperature for 18 hours
6. 6
   OtherThe reaction is then evaporated to dryness, residue
7. 7
   workup.DISSOLUTIONdissolved in hexanes
8. 8
   Washwashed with water (100 mL)
9. 9
   OtherThe hexanes phase is separated
10. 10
    Dryingdried with Na2SO4
11. 11
    Filtrationfiltered
12. 12
    Otherevaporated to dryness

Procedure

To a flame dried, 500 mL round bottomed flask equipped with an addition funnel charged with epichlorohydrin (15.62 g, 0.17 moles), is added 2-ethylhexanol (16.5 g, 0.127 moles) and stannic chloride (0.20 g, 0.001 moles). The reaction is kept under an argon atmosphere and warmed to 90° C. using an oil bath. Epichlorohydrin is dripped into the stirring solution over 60 minutes followed by stirring at 90° C. for 18 hours. The reaction is fitted with a vacuum distillation head and 1-chloro-3-(2-ethyl-hexyloxy)-propan-2-ol is distilled under 0.2 mm Hg. The 1-chloro-3-(2-ethyl-hexyloxy)-propan-2-ol (4.46 g, 0.020 moles) is dissolved in tetrahydrofuran (50 mL) and stirred at room temperature under an argon atmosphere. To the stirring solution is added potassium tert-butoxide (2.52 g, 0.022 moles) and the suspension is stirred at room temperature for 18 hours. The reaction is then evaporated to dryness, residue dissolved in hexanes and washed with water (100 mL). The hexanes phase is separated, dried with Na2SO4, filtered and evaporated to dryness to yield the crude 2-ethylhexyl glycidyl ether, which can be further purified by vacuum distillation.

Source