3-Methyl-2-buten-1-OL → 3,3-Dimethylallylglycidyl ether
Reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][OH:5].[H-].[Na+].[CH2:9]([CH:11]1[O:13][CH2:12]1)Br>O1CCCC1>[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][O:5][CH2:9][CH:11]1[O:13][CH2:12]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3,3-dimethylallyl alcohol (17.3 g, 20.5 mL, 0.2 mol) in dry tetrahydrofuran (THF) (200 mL) was added sodium hydride (4.8 g, 0.2 mol) in portions and the mixture was stirred at room temperature for 1 hr. Epibromohydrin (27.4 g, 17.12 mL, 0.2 mol) was added dropwise and the reaction mixture was stirred at room temperature for 24 hrs. 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. bp: 93°-94° C./10 mm. Yield: 17.2 g (60.5%). 1H NMR (CDCl3) ε 1.68 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).