Esterification Reaction

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Alexi999
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Esterification Reaction

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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
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ChenBeier
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Re: Esterification Reaction

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First it's not a ester. Ester made from acid and alcohol.
What you talking about is a mixed acid anhydride.

To get this take acetylchloride CH3COCl and disodium hydrogen phosphate Na2HPO4.

CH3COCl + Na2HPO4 => CH3CONaHPO4 + NaCl
Alexi999
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Re: Esterification Reaction

Post by Alexi999 »

Thank you for the reply!
I thought that an acid anhydride is a compound that has two acyl C(O)R groups bonded to the same oxygen atom.

Thanks for the clarification. I'm still learning.

Also, what prevents di-linkage at both sodium positions of the phosphate by acetylchloride?
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Re: Esterification Reaction

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The stoechometric mixture of the reactants guid to it. Probably take more of the phosphate.

Anhydride means remove water. The anhydride can made by 2 CH3COOH => (CH3CO)2O + H2O but also with different acids.

CH3COOH + C2H5COOH => CH3CO(C2H5CO)O + H2O

H3PO4 + CH3COOH => CH3COH2PO4 + H2O
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Re: Esterification Reaction

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Ok so treat the carboxylic acid with thionyl chloride ( SOCl2 ) to form the intermediate acid chloride in aqueous solution

Neutralize with NaOH

Then simply stoichiometrically add the disodium phosphate (Na2HPO4)

Then collect precipitate final product .

(What ratio of H2O to the CH3COOH do you suggest for optimal reactivity?)
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ChenBeier
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Re: Esterification Reaction

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You can not use aqueous solution. SOCl2 either CH3COCl will decompose in presence of water.
Why to produce acetylchloride from acetic acid and thionylchloride, from cost side buy directly acetylchloride and add it to the dry phosphate.
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Re: Esterification Reaction

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So what if I want to use a different carboxylic acid, so what would be the system to do this
if I can't buy a chlorinated acid form?
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Re: Esterification Reaction

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So for example could I use sulfuric acid in aqueous solution to functionalize the carbonyl to
(CH3COOH + NaH2PO4) cat H2SO4 -> CH3CONaHPO4 +H2O
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Re: Esterification Reaction

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I'm just confused on how to go about this.
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Re: Esterification Reaction

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No, the product is water sensitive. The Anhydride will decompose if in contact with water. Sulfuric acid will any way convert the phosphate to phosphoric acid.
You can only make it in absense of water.
Of course if you cannot buy the chlorinated Acyl ,then you have to do the chlorination first.
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Re: Esterification Reaction

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Yes, can you tell me the optimal route for this chlorination, for a full synthesis.
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ChenBeier
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Re: Esterification Reaction

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You already chosed it. Thionylchlorid SOCl2, but also phosphorous trichloride PCl3 or phosphorous oxychloride POCl3 are possible.
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Re: Esterification Reaction

Post by Alexi999 »

Thanks for you help. 😁
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Re: Esterification Reaction

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