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

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Charlie

28. uMfumfu 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.
Osezingeni eliphezulu
1 day

Imiyalelo

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.

Izinto zokwakha zalesi sinyathelo:

I-ketene dimerI-ketene dimer1 as required
I-anilineI-aniline1 as required

Amathuluzi adingekayo:

Ibhodlela elinesisekelo esiyindilingaIbhodlela elinesisekelo esiyindilinga
Induku Yengilazi YokugovuzaInduku Yengilazi Yokugovuza
Ikhabethe lomusi (elinepayipi)Ikhabethe lomusi (elinepayipi)
Amagilavu E-nitrileAmagilavu E-nitrile
Izibuko Zokuchitheka KwamakhemikhaliIzibuko Zokuchitheka Kwamakhemikhali
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.

Amathuluzi adingekayo:

I-ethanol - izinga lelabhorethri, 95 %I-ethanol - izinga lelabhorethri, 95 %
AmanziAmanzi
Ipuleti ElishisayoIpuleti Elishisayo
I-funnel ye-Büchner (i-porcelain)I-funnel ye-Büchner (i-porcelain)
Amagilavu E-nitrileAmagilavu E-nitrile

Izinto

2
  • 1
    I-ketene dimer
    1 as required
    Isibambeli
  • 1
    I-aniline
    1 as required
    Isibambeli

Amathuluzi Adingekayo

9

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I-acetoacetanilide

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

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

ngu-CharlieDE

Organic

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

Aniline: Nitrobenzene Reduced with Iron and Acid, Cain 1919

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Organic

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