3-Methyl-2-buten-1-OL → 3,3-Dimethylallylglycidyl ether

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).

1. stirringthe reaction mixture was stirred at room temperature for 24 hrs
2. customTHF was removed on a rotary evaporator
3. filtrationfiltered
4. concentrationThe ether solution was concentrated on a rotary evaporator
5. customthe brown oil obtained
6. distillationwas distilled under vacuum

ORD record

ord-25c92661dbef4bdeba198ec9a5fca83c

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05627286