Mono-esterify a mono-phosphate salt group to a carboxylic acid

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Discussion Overview

The discussion revolves around the synthesis of a mono-esterified mono-phosphate salt group with a carboxylic acid, specifically focusing on the reaction between acetic acid and sodium dihydrogen phosphate. Participants explore methods for facilitating the resultant product and potential synthesis routes.

Discussion Character

  • Exploratory, Technical explanation, Debate/contested

Main Points Raised

  • One participant inquires about the easiest method to mono-esterify a mono-phosphate salt group to a carboxylic acid.
  • Another participant suggests researching "acetyl phosphate preparation," noting that the compound is typically prepared through transesterification of an organic acetate with phosphoric acid, rather than directly from acetic acid.
  • The same participant mentions that while the direct reaction might work under certain conditions, the optimization of the reaction likely occurs during the separation and workup stages.
  • A follow-up request for an optimal synthesis route is made, indicating a desire for more specific guidance.
  • A subsequent reply expresses that the responder cannot provide a better synthesis route than what can be found through a search engine.

Areas of Agreement / Disagreement

Participants do not reach a consensus on a specific synthesis route, and multiple approaches to the problem are suggested without resolution.

Contextual Notes

The discussion does not clarify specific conditions or parameters for the reactions mentioned, leaving assumptions about reaction conditions and optimization unresolved.

Who May Find This Useful

Researchers or students interested in organic synthesis, particularly those focused on esterification reactions and phosphate chemistry.

Alexander Roschinkov
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TL;DR
Organic Chemistry
I am interested to see if anyone knows the easiest way to mono-esterify a mono-phosphate salt group to a carboxylic acid.

How to facilitate the resultant -> product ?

CH3COOH + NaH2PO4 ‐> C2H4NaO5P + H20
Screenshot_20211017-151346_Molecular Constructor.jpg
 
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You can google “acetyl phosphate preparation” to get several results on how the compound is prepared commercially. Generally, it goes through a transesterification of an organic acetate with phosphoric acid, rather than a direct reaction of acetic acid with a phosphate, though the latter will probably work at least a little bit under the right conditions. The compound itself isn’t likely to be particularly difficult to make, but the separation/isolation/general workup is probably where most of the optimization of the reaction happens.
 
Thanks for the response,
Would you happen to have an optimal route to synthesis?
 
Alexander Roschinkov said:
Thanks for the response,
Would you happen to have an optimal route to synthesis?
I’m not going to be able to do better than a google search can.
 
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Thanks
 

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