Hydrochloric Acid → Octyl Maleimide

Participants

Reaction Conditions

Reaction Steps

To a suspension of maleic anhydride (54, 5.4 g, 55 mmol) in 150 ml of benzene, a solution of octyl amine (53, 6.46 g, 50 mmol) in 100 ml of benzene was added. The resulting mixture was stirred at 30° C. for an hour and ZnBr2 (12.4 g, 55 mmol) and hexamethyl disilazane (12.1 g, 75 mmol) in 30 ml of benzene were added. The resulting suspension was refluxed for 2 hrs. After cooling to room temperature, the reaction mixture was poured into 200 ml of 0.5 M HCl. The organic layer was separated and the aqueous portion was extracted twice with 150 ml portions of EtOAc. The combined organic layers were washed with saturated aqueous NaHCO3 (2×150 ml), brine (1×150 ml), and dried over Na2SO4. The solution was dried under vacuum to yield an oily product which solidified gradually to yield the cream colored solid product (9.2 g, 88%). 1H NMR (300 MHz, CDCl3): δ 0.87 (t, 3H, J=6 Hz), 1.20-1.40 (m, 10H), 1.50-1.70 (m, 2H), 3.51 (t, 2H, J=6 Hz), 6.69 (s, 2H).

Provenance & Evidence