Acetoacetanilide [102-01-2-A] C10H11NO2
In a 1000-ml three-neck round-bottom flask, mix 153 ml of ethyl acetoacetate, 500 ml of toluene, and 0.5 ml of pyridine. Equip the flask with a dropping funnel, thermometer up to 200 °C, and a descending distillation bridge with a receiver. Heat the flask contents to a gentle boil and add a mixture of 91 ml of aniline, 500 ml of toluene, and 0.5 ml of pyridine dropwise over 5 hours, ensuring that approximately the same amount of toluene distills off as the solution is added. After all the solution has been added, replace the distillation bridge with a reflux condenser and heat the reaction mixture under reflux for 2 hours. The solution should then have a pale yellow color but not red. Pour the still warm solution into an 800-ml beaker, where acetoacetanilide precipitates upon cooling. Sometimes acetoacetanilide only precipitates upon seeding. After 12 hours of rest, filter off the product, wash with 50 ml of toluene, and dry in a drying oven at 60 °C. The yield is 150 g of a product melting at 85 °C. This corresponds to 85% of the theoretical yield.
Description: Acetoacetanilide forms a white, water-insoluble powder. The substance couples at the reactive methylene group with diazonium salts to form mostly insoluble azo dyes and is therefore used in the chemical industry for the production of pigments (e.g., Hansayellow G) for the paint industry.
Source: Fierz-David, Blangey, Fundamental Operations of Color Chemistry, 5th Edition, Vienna 1943, p. 137
Delivered by: Mephisto
Last updated: 19/06/2006
Other names: Acetoacetic acid anilide; 3-Oxo-N-phenylbutanamide; 3-Oxo-N-phenylbutyric acid amide