Acetic Acid → 3-(3-Acetamidophenyl)prop-2-enoic acid

Participants

Reaction Steps

Tin II chloride dihydrate (170 g, 0.75 mol) was dissolved in concentrated HCl (200 mL). Warming was necessary to obtain a clear solution. 3-Nitrocinnamic acid (35 g, 0.181 mol) was added portionwise with stirring. After about 20% of the 3-nitrocinnamic acid had been added, the mixture was warmed with a heat gun to 45° C. to initiate reaction. The rate of addition was controlled to maintain a temperature of 65-75° C. The reaction was exothermic, but not vigorous on this scale. After the addition was complete, and the reaction started to subside, the flask was transferred to an oil bath at 65° C. for 1 h. The mixture was then cooled to room temperature. The solid was filtered, washed with 2 N HCl, (100 mL) and sucked dry. The filter cake was dried in a vacuum oven for 1 h, then in air overnight, to give about 65 g of the crude amine. This material was suspended in acetic acid (300 mL) and acetic anhydride (150 mL, 1.6 mol) was added gradually with stirring. After the initial exotherm subsided, the mixture was stirred in an oil bath at 110° C. for 2 h, resulting in a clear solution. LCMS showed complete conversion to the desired acetanilide. The solution was cooled and water (50 mL) was added. After standing overnight the solution was concentrated to about 300 mL. More water (100 mL) and 2 N HCl (50 mL) were added. The precipitate was filtered, washed with water and dried to give 3-acetamido cinnamic acid (33.2 g, 89%).

Provenance & Evidence