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Acetoacetanilide: Ketene Dimer Combined with Aniline (Thorpe 1912)
The ketene dimer combines with aniline to give acetoacetanilide.
Source: Thorpe, Dictionary of Applied Chemistry vol. 3 (1912), Ketenes. Unknown: the amounts and the conditions. Thorpe states only that the two combine. The isolation is ours, after Organic Syntheses Coll. Vol. 3, p. 10 (1955). Picture drawn by Youblob.
Advanced
1 day
Instructions
1
1
Combine the dimer with aniline
Combine the dimer with aniline
Bring the ketene dimer together with aniline: they combine to form acetoacetanilide. Unknown: the amounts and conditions. Ours: gloves and a fume hood.
Materials for this step:
Ketene Dimer1 as required
Aniline1 as requiredTools needed:
Round-Bottom Flask
Glass Stirring Rod
Fume Hood (Ducted)
Nitrile Gloves
Chemical Splash Goggles2
2
Isolate the acetoacetanilide
Isolate the acetoacetanilide
Ours, after Organic Syntheses Coll. Vol. 3, p. 10 (1955): dissolve the crude product in hot 50 % aqueous ethanol (they used 500 ml for the product of 0.5 mole aniline), cool to 0 °C and filter. Adding water to the mother liquor (250 ml) and cooling again gives a second crop. It melts at 82-83.5 °C; recrystallised from 50 % ethanol, at 84-85 °C.
Tools needed:
Ethanol - Lab Grade, 95%
Water
Hot Plate
Buchner Funnel (Porcelain)Nitrile GlovesTools Required
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