Ethanol → Aniline, N,N-diallyl- (8CI)

Temperature

19 °C

To a stirred solution of aniline (5.62 g, 60.36 mmol) in EtOH (200 ml) and water (50 ml) was added allyl bromide (17.33 g, 143.3 mmol) in one portion followed by solid Na2CO3 (6.69 g, 62.5 mmol). The yellow mixture was then heated under reflux for 17 h, left to cool to room temperature (19° C.) and the EtOH was removed under reduced pressure. The aqueous residue was extracted with Et2O (5×200 ml) and the combined organics were washed with brine (3×200 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give a brown oil that was distilled over KOH pellets to give the title compound (7.81 g, 75%) as a pale yellow oil.

1. temperatureThe yellow mixture was then heated
2. temperatureunder reflux for 17 h
3. waitleft
4. customthe EtOH was removed under reduced pressure
5. extractionThe aqueous residue was extracted with Et2O (5×200 ml)
6. washthe combined organics were washed with brine (3×200 ml)
7. dry with materialdried (Na2SO4)
8. customThe solvent was removed under reduced pressure
9. customto give a brown oil that
10. distillationwas distilled over KOH pellets

ORD record

ord-e0dfc0b5dd104e9d958255f181956b88

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691979B2