Meldrum's acid

- Sep 21, 2018 -

Meldrum's Acid
Meldrum's Acid
Chemical name2,2-Dimethyl-1,3-dioxane-4,6-dione
Chemical formulaC6H8O4
Molecular mass144.1253 g/mol
CAS number[2033-24-1]
Density? g/cm3
Melting point94-96 °C
Boiling point? °C
Disclaimer and references

Meldrum's acid or 2,2-dimethyl-1,3-dioxane-4,6-dione is an organic compound. The main ring structure is a dioxane. The compound was discovered in 1908 by A.N. Meldrum 1 and it is prepared by a condensation reaction of malonic acid with acetone in acetic anhydride with sulfuric acid. Meldrum misidentified 2 the structure as a beta-lactone with a fully fledged carboxylic acid group. Yet Meldrum's acid has a high acidity with a pKa of 4.97, because like ascorbic acid, deprotonation at the methylene next tothe carbonyls produces a stable enolate. Because of this property Meldrum's acid like malonic acid is a reactant in Knoevenagel condensations.

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