2',5'-Dimethoxyacetoacetanilide [6375-27-5-A] C12H15NO4
In a 500-ml three-neck flask, dissolve 100 g of 2,5-Dimethoxyaniline in 250 ml of benzene. Equip the flask with a stirring bar, reflux condenser, dropping funnel, and thermometer (up to 100 °C). Fill the dropping funnel with 50 ml of diketene. Subsequently, heat the contents of the flask in a water bath to 40 °C and start adding the diketene dropwise once the temperature is reached. Once all the diketene has been added, heat the reaction mixture to a vigorous boil for an additional 40 minutes. After cooling, the precipitated product is filtered off, washed with water, and dried in a vacuum desiccator. The yield of 2',5'-Dimethoxyacetoacetanilide is 94% of the theoretical amount.
Description: 2',5'-Dimethoxyacetoacetanilide forms a white, water-insoluble powder. The substance couples at the reactive methylene group with diazonium salts to form mainly insoluble azo dyes and is therefore used in the chemical industry for the production of pigments for the paint industry.
Source: Kaslow, Sommer, J. Am. Chem. Soc., 68, 1946, 644-647
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Last updated: 19/06/2006
Other names: Acetoacetyl-2,5-dimethoxyanilide; N-(2,5-Dimethoxyphenyl)-3-oxo-butanamide; N-(2,5-Dimethoxyphenyl)-3-oxo-butyramide; NSC 50634