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Acetoacetanilide: Ketene Dimer Combined with Aniline (Thorpe 1912)
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Charlie

28. Ukwakira 2026DE
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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.
Hejuru
1 day

Amabwiriza

1

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.

Ibikoresho by'iyi ntambwe:

Dimeri ya keteneDimeri ya ketene1 as required
AniliniAnilini1 as required

Ibikoresho bikenewe:

Icupa rifite igituza kizengurutseIcupa rifite igituza kizengurutse
Akati k'Ikirahure ko KuvangaAkati k'Ikirahure ko Kuvanga
Akabati k'umwotsi (gafite umuyoboro)Akabati k'umwotsi (gafite umuyoboro)
Uturindantoki twa NitirileUturindantoki twa Nitirile
Amadarubindi yo Kwirinda IbinyabutabireAmadarubindi yo Kwirinda Ibinyabutabire
2

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.

Ibikoresho bikenewe:

Etanoli - urwego rw'ubushakashatsi, 95 %Etanoli - urwego rw'ubushakashatsi, 95 %
AmaziAmazi
Urubaho rushyushyaUrubaho rushyushya
Ifonelo ya Büchner (ya porcelaine)Ifonelo ya Büchner (ya porcelaine)
Uturindantoki twa NitirileUturindantoki twa Nitirile

Ibikoresho

2
  • 1
    Dimeri ya ketene
    1 as required
    Umwanya
  • 1
    Anilini
    1 as required
    Umwanya

Ibikoresho bikenewe

9

Iki gishushanyo gikora

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Asetoasetanilide

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Ketene Dimer: Ketene Left to Polymerise, the 126-127 °C Liquid (Thorpe 1912)
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Ketene Dimer: Ketene Left to Polymerise, the 126-127 °C Liquid (Thorpe 1912)

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Aniline: Nitrobenzene Reduced with Iron and Acid, Cain 1919
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Aniline: Nitrobenzene Reduced with Iron and Acid, Cain 1919

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