Allyl iodide → 3-(2-Ethylphenyl)-1-propene

Temperature

50 °C

To a suspension of 8.53 g (350 mmoles) of magnesium in 270 mL in dry tetrahydrofuran was added 50 g (270 mmol) of 1-bromo-2-ethylbenzene. The temperature was maintained at 50° C. during addition, then was heated under reflux. After 1 h, the solution was cooled to -78° C. under N2, and 54.42 g (324 mmoles) of allyl iodide was added dropwise. The mixture was allowed to warm to room temperature, stirred for an additional 2 h, then cooled to 0° C. The reaction was quenched by addtition of 2M HCl and 500 mL of ether and the layers were separated. The organic layer was washed with 30 mL of saturated NaHCO3 solution and brine, dried over MgSO4, and concentrated. The oily residue was filtered through silica gel with 20% ethyl acetate-hexane and the eluate was concentrated to afford the crude 1-allyl-2-ethylbenzene as a colorless oil.

1. temperaturewas heated
2. temperatureunder reflux
3. temperaturethe solution was cooled to -78° C. under N2
4. temperatureto warm to room temperature
5. temperaturecooled to 0° C
6. customThe reaction was quenched by addtition of 2M HCl and 500 mL of ether
7. customthe layers were separated
8. washThe organic layer was washed with 30 mL of saturated NaHCO3 solution and brine
9. dry with materialdried over MgSO4
10. concentrationconcentrated
11. filtrationThe oily residue was filtered through silica gel with 20% ethyl acetate-hexane
12. concentrationthe eluate was concentrated

ORD record

ord-118b562d2b8c4b74a7063e52774b1329

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06100293