反应详情

温度

2.5 °C

4-octylbenzaldehyde (10.0 g, 45.8 mmol) (Aldrich) was dissolved in THF (229 ml) under nitrogen. The reaction was cooled to about 0-5° C. in an ice bath. A solution of allylmagnesium bromide (48.1 ml, 48.1 mmol) (Aldrich) was added slowly and the reaction stirred for about 2 h. The reaction was quenched by the addition of saturated ammonium chloride followed by addition of ethyl acetate. The layers were separated and the aqueous extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered, and evaporated to an off-white oil. The residue was dissolved in ether and dried over sodium sulfate and filtered. The solvents were removed under reduced pressure to provide 1-(4-octylphenyl)but-3-en-1-ol (11.54 g, 44.3 mmol, 97% yield) as a light yellow oil: LC/MS (method f) Rt=2.90 min.; MS m/z: 243.21 (M-water)+.

1. customThe reaction was quenched by the addition of saturated ammonium chloride
2. additionfollowed by addition of ethyl acetate
3. customThe layers were separated
4. extractionthe aqueous extracted with ethyl acetate
5. washThe combined extracts were washed with brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customevaporated to an off-white oil
9. dissolutionThe residue was dissolved in ether
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. customThe solvents were removed under reduced pressure