What Solid Separates During the Malonic Ester Synthesis Reaction?

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Discussion Overview

The discussion revolves around the solid that separates during the malonic ester synthesis reaction involving urea and diethyl n-butylmalonate in the presence of sodium ethoxide. Participants explore various hypotheses regarding the identity of the solid product formed after mixing and heating the reactants.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested

Main Points Raised

  • One participant suggests that the solid could be diethyl n-butylmalonate, modified by the loss of one acidic hydrogen due to the sodium ethoxide, questioning why this would remain unreacted.
  • Another participant proposes that the solid might be the sodium salt of butylbarbituric acid.
  • A third participant references a paper by Dox and Yoder, indicating that the solid is ammonium chloride, assuming the reaction is conducted in ethanol.
  • A later reply raises a concern about the nature of the synthesis, suggesting it may involve controlled substances, which could be problematic within the forum context.

Areas of Agreement / Disagreement

Participants express differing views on the identity of the solid that separates, with no consensus reached. Multiple hypotheses are presented, and the discussion remains unresolved.

Contextual Notes

Participants reference a specific paper for clarification, indicating that the answer may depend on the conditions of the reaction, such as the solvent used. There is also an implication that the synthesis may be sensitive to regulatory considerations.

ericvon11
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So I'm performing the reaction using:

urea + diethyl n-butylmalonate ----NaOEt---> n-butylbarbituric acid

My question is, after adding everything, you mix it and heat it, what is the solid that separates during this reaction? I've been thinking it might be diethyl n-butylmalonate but without 1 acid hydrogen due to the NaOEt. Why would this be unreacted though? ANY thoughts or advice would be greatly appreciated
 
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How about the sodium salt of the butylbarbituric acid?
 
There is a paper by Arthur W Dox and Lester Yoder called "Alkylbenzene Barbituric Acids." This was published in JACS in 1922. I found the answer in the experimental section. Look up the paper and give it a read.

I'm not trying to make you sweat... If you don't respond by tomorrow, I'll just post it here for completeness :)

EDIT: Didn't realize this was posted so long ago. Anyway... According to the paper, it's ammonium chloride. I assume you're running this reaction in ethanol.
 
It looks like you're talking about the non-professional synthesis of something which is either a controlled substance or pretty darned close to being a controlled substance... which is probably frowned upon by the admins around here.
 

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