1-Bromooctane → HCID 22468237, compound

To a stirring solution of diethylmalonate (16.0 g, 100 mmol) in THF (200 mL, 0.5 M) was added sodium hydride (2.4 g, 100 mmol). The solution began bubbling and an exothermic reaction occurred. The reaction eventually turned clear and then octyl bromide (17.3 mL, 100 mmol) was added. The reaction was refluxed for 20 hours and then cooled to room temperature. Another equivalent of NaH (2.4 g, 100 mmol) was added to the cloudy white mixture which was then stirred for 4 hours at room temperature. Another equivalent of octyl bromide (17.3 mL, 100 mmol) was added and the reaction was refluxed for 20 hours. The reaction was cooled to room temperature and filtered (NaBr). The mother liquor was collected and concentrated in vacuo to a yellow oil. The crude product was then distilled under vacuum (250° C.) to afford 23.4 g (64%) of pure product.

1. customThe solution began bubbling
2. customan exothermic reaction
3. customThe reaction eventually turned clear
4. temperatureThe reaction was refluxed for 20 hours
5. temperaturethe reaction was refluxed for 20 hours
6. temperatureThe reaction was cooled to room temperature
7. filtrationfiltered (NaBr)
8. customThe mother liquor was collected
9. concentrationconcentrated in vacuo to a yellow oil
10. distillationThe crude product was then distilled under vacuum (250° C.)

ORD record

ord-68ce3a44c8b8429e9fb4c313839eb303

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06297400B1