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

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) δ 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 mixture was stirred at room temperature for 24 hours
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-5707fc1dbc224fb1a0be0b9455aef82a

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05688487