morsagh
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Mixed carboxylic-phosphoric acid anhydride
How can be mixed carboxylic-phosphoric acid anhydride (like 1,3-bisphosphoglycerate) prepared synthetically? For example if i want to produce
phosphoacetic anhydride i can´t just boil phosphoric acid with acetic because normal acetic anhydride is produced, so are there any other ways? Thank
you for help
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Kagutsuchi
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It is mere speculation, but maybe it can be produced by the carbonylation of organic alcohol-phosphoric acid-esters, for example the phosphoacetic
anhydride could be produced from methyl-phosphate.
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DraconicAcid
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If we're going to speculate, I would guess the reaction of acetic acid with POCl3.
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morsagh
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I think POCl3 with carboxylic acid produce just acyl chloride? Carbonylation seems very extreme to try... No studies about preparation of these
anhydrides?
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Nicodem
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Thread Moved
12-1-2016 at 09:57 |
UC235
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There's literature on them, but it is fairly scarce. A search for a model compound, acetylphosphoric acid (acetyl phosphate) gives this paper which
uses ketene and phosphoric acid.
https://gmwgroup.harvard.edu/pubs/pdf/69.pdf
The references list contains preps using acetyl chloride, namely http://www.jbc.org/content/153/2/571.full.pdf
Acetyl chloride and Silver Diammonium Phosphate give ~70% yield isolated as the silver salt.
Isopropenyl acetate can be coaxed into reacting with phosphoric acid in the presence of sulfuric acid to gives 60-70% yield isolated as dilithium
acetylphosphate.
http://www.jbc.org/content/185/2/549.full.pdf
An excess of acetic anhydride reacts with triethylammonium dihydrogen phosphate to give acetyl phosphate which is isolated as the dilithium salt. No
yield seems to be given, but it is substantially free of contaminating inorganic phosphate.
http://www.jbc.org/content/244/7/1846.full.pdf
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