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

Participants

Reaction Conditions

Reaction Steps

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:

Provenance & Evidence