Reaction #75447

Reaction equation

Epibromohydrin

dimethylallyl alcohol

sodium hydride

→

title product

3,3-Dimethylallylglycidyl Ether

Solvents

THF

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 24 hours
2. 2
   OtherTHF was removed on a rotary evaporator
3. 3
   Filtrationfiltered
4. 4
   ConcentrationThe ether solution was concentrated on a rotary evaporator
5. 5
   Otherthe brown oil obtained
6. 6
   workup.DISTILLATIONwas distilled under vacuum

Procedure

To a solution of dimethylallyl alcohol (17.3 g, 20.5 mL, 0.2 mol) in dry THF (200 mL), sodium hydride (4.8 g, 0.2 mol) was added in portions and the mixture was stirred at room temperature for 1 hour. Epibromohydrin (27.4 g, 17.12 mL, 0.2 mol) was added to this reaction mixture dropwise and the mixture was stirred at room temperature for 24 hours. THF was removed on a rotary evaporator and the residue was taken up in ether and filtered. The ether solution was concentrated on a rotary evaporator and the brown oil obtained was distilled under vacuum to yield the title product. bp. 93-94° C./10 mm. Yield: 17.2 g (60.5%). 1H NMR (CDCl3) δ1.68 and 1.75 (s, 6H, CH3), 2.61 and 2.88 (dd,2H, oxirane CH2), 3.17 (m, 1H, oxirane CH), 3.38 and 3.7 (m, 2H, CH2OCH2CH), 4.05 (m, 2H, CH2OCH2CH), 5.35 .(m, 1H, >C═CH).

Source