Hydrochloric Acid → p-Octylphenylboric acid

Temperature

-78 °C

50 ml of THF (tetrahydrofuran) was added to 2.91 g (0.12 mol) of metallic magnesium, and the mixture was stirred. 100 ml of a solution of 26.89 g (0.1 mol) of p-octylbromobenzene in THF was added dropwise thereto, and the mixture was heated. After the initiation of the reaction was confirmed, the mixture was refluxed for one hr. The mixture was cooled to −78° C., 12.46 g (0.12 mol) of trimethylboric acid was added dropwise thereto, and the mixture was stirred for 30 min. The temperature was returned to room temperature, followed by stirring for additional one hr. Dilute hydrochloric acid was added thereto, and the mixture was stirred for one hr. The aqueous layer was extracted with ether, and the oil layer was washed with water and then with an aqueous sodium hydrogencarbonate. The oil layer was then dried over sodium sulfate, the solvent was removed by distillation, and the resultant crude product was purified by chromatography on silica gel to give p-octylphenylboric acid.

1. temperaturethe mixture was heated
2. temperaturethe mixture was refluxed for one hr
3. stirringthe mixture was stirred for 30 min
4. customwas returned to room temperature
5. stirringby stirring for additional one hr
6. stirringthe mixture was stirred for one hr
7. extractionThe aqueous layer was extracted with ether
8. washthe oil layer was washed with water
9. dry with materialThe oil layer was then dried over sodium sulfate
10. customthe solvent was removed by distillation
11. customthe resultant crude product was purified by chromatography on silica gel

ORD record

ord-dbec040289ef4a3ba7dcd60cd7963b48

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06174455B1