Benzyl Bromide → HCID 10420947, compound

Temperature

25 °C

A solution of 3(S)-hydroxy-1-octene (6.41 g., 0.05 mole) in dry dimethylformamide is added dropwise to a stirred suspension of hexane (2 × 10 ml.) -- prewashed sodium hydride (50% dispersion in mineral oil, 2.64 g., 0.055 mole) in dry dimethylformamide (45 ml.) at 25° C. Upon cessation of gas evolution, the reaction mixture is cooled to 0° to 5° C. and treated with a solution of benzyl bromide (10.3 g., 0.06 mole) in dry dimethylformamide (10 ml.). The resulting mixture is stirred at 25° C. for 16 hours, then is heated at 100° C. for 1 hour. After cooling to 25° C., the reaction mixture is diluted with ice water (50 ml.) and extracted with ether four times. The combined organic extract is washed with 2N hydrochloric acid and saturated aqueous brine, dried over magnesium sulfate and filtered. In vacuo evaporation of the filtrate leaves an oily residue which affords the title compound upon distillation as a colorless oil.

1. customat 25° C
2. temperatureUpon cessation of gas evolution, the reaction mixture is cooled to 0° to 5° C.
3. temperatureis heated at 100° C. for 1 hour
4. temperatureAfter cooling to 25° C.
5. extractionextracted with ether four times
6. extractionThe combined organic extract
7. washis washed with 2N hydrochloric acid and saturated aqueous brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. customIn vacuo evaporation of the filtrate
11. customleaves an oily residue which

ORD record

ord-599268b58bfc48588eddced469e73c32

Source dataset

uspto-grants-1977_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04022794