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Acetoacetanilide: Aniline in Ether with Diketene Added Slowly (Gleason, Standard Oil Development, US 2,174,239)
Diketene and aniline join into acetoacetanilide, the coupling component of Hansa yellow, but neat they react so violently that the product is poor. Gleason tamed the reaction by diluting both in ether and adding the diketene slowly; the anilide simply crystallises out.
Result: crystals of acetoacetanilide.
Source: Gleason, US 2,174,239 (Standard Oil Development, 1939). Not given: yield. Picture drawn by Youblob.
Intermediate
1 day
Instructions
1
1
Dissolve the aniline
Dissolve the aniline
Dissolve 1 part by weight of aniline in about 5 parts of ether at room temperature.
Materials for this step:
Aniline1 part by weightTools needed:
Diethyl Ether
Round-Bottom Flask
Balance Scale2
2
Add diketene slowly
Add diketene slowly
Add 1 part of diketene slowly with stirring. Keep it at room temperature or a little above, never even locally above 80-100 C; cool if needed.
Materials for this step:
Ketene Dimer1 part by weightTools needed:
Separatory Funnel
Thermometer3
3
Let it crystallise
Let it crystallise
When the reaction is over, let the liquid stand; acetoacetanilide crystallises.
Tools needed:
Round-Bottom Flask4
4
Collect and wash
Collect and wash
Decant or filter off the crystals and wash them with a little cold ether.
Tools needed:
Buchner Funnel (Porcelain)
Filter PaperDiethyl EtherTools Required
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