Reaktion #1772000

Reaktionsgleichung

Epichlorohydrin

potassium tert-butoxide

epichlorohydrin

2-propylheptanol

1-chloro-3-(2-propyl-heptyloxy)-propan-2-ol

1-chloro-3-(2-propyl-heptyloxy)-propan-2-ol

→

2-propylheptyl glycidyl ether

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a flame dried
2. 2
   Sonstige500 mL round bottomed flask equipped with an addition funnel
3. 3
   workup.DISTILLATIONis distilled at a temperature range of 90° C.->95° C. under 0.2 mm Hg
4. 4
   workup.STIRRINGstirred at RT under an argon atmosphere
5. 5
   workup.STIRRINGthe suspension is stirred at RT for 18 hours
6. 6
   SonstigeThe reaction is then evaporated to dryness, residue
7. 7
   workup.DISSOLUTIONdissolved in hexanes
8. 8
   Waschenwashed with water (100 mL)
9. 9
   SonstigeThe hexanes phase is separated
10. 10
    Trocknendried with Na2SO4
11. 11
    Filtrationfiltered
12. 12
    Sonstigeevaporated to dryness

Vorschrift

To a flame dried, 500 mL round bottomed flask equipped with an addition funnel charged with epichlorohydrin (15.62 gm., 0.17 moles), is added 2-propylheptanol (Pfaltz & Bauer, Inc., 172 E. Aurora Street, Waterbury Conn., 06708, USA) (20 gm., 0.127 moles) and stannic chloride (0.20 gm., 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-propyl-heptyloxy)-propan-2-ol is distilled at a temperature range of 90° C.->95° C. under 0.2 mm Hg. Wt.=22.1 gm. The 1-chloro-3-(2-propyl-heptyloxy)-propan-2-ol (5.0 gm., 0.020 moles) is dissolved in tetrahydrofuran (50 mL) and stirred at RT under an argon atmosphere. To the stirring solution is added potassium tert-butoxide (2.52 gm., 0.022 moles) and the suspension is stirred at RT 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-propylheptyl glycidyl ether, which can be further purified by vacuum distillation.

Quelle