Acetic Acid → 2,4-Bis(propan-2-yl)aniline

Mossey Tin (22 g, 184.5 mmol) was added to a solution of Intermediate 32 (25 g, 120 mmol), followed by conc. HCl (150 mL). After heating at 100° C. for 1 hour, acetic acid (50 mL) was added to the mixture and it was heated for another 30 minutes. After stirring at room temperature overnight, the reaction mixture was diluted with ether (500 mL), washed with water (50 mL) and transferred to a 500 mL beaker. Solid potassium carbonate was carefully added until all acids were quenched (˜80 g). The mixture was then extracted with ether (3×100 mL), washed with brine (1×20 mL), dried (Na2SO4) and concentrated to give the title compound in a crude form as a brown oil that was taken to the next step without further purification:

1. temperaturewas heated for another 30 minutes
2. washwashed with water (50 mL)
3. additionSolid potassium carbonate was carefully added until all acids
4. customwere quenched (˜80 g)
5. extractionThe mixture was then extracted with ether (3×100 mL)
6. washwashed with brine (1×20 mL)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated

ORD record

ord-adbb901b9053474598c0081109eb7756

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06936636B2