Meldrum's acid
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| Meldrum's Acid | |
|---|---|
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| Chemical name | 2,2-Dimethyl-1,3-dioxane-4,6-dione |
| Chemical formula | C6H8O4 |
| Molecular mass | 144.1253 g/mol |
| CAS number | [2033-24-1] |
| Density | ? g/cm3 |
| Melting point | 94-96 °C |
| Boiling point | ? °C |
| SMILES | O=C(C1)OC(C)(C)OC1=O |
| 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 to the carbonyls produces a stable enolate. Because of this property Meldrum's acid like malonic acid is a reactant in Knoevenagel condensations.
[edit] External links
- Synlett Spotlight Website
- Meldrum's acid in Organic Syntheses Website
[edit] References
- 1 Meldrum, A. N. J. Chem. Soc. 1908, 93, 598.
- 2 The Structure of Meldrum's Supposed beta-Lactonic Acid David Davidson, Sidney A. Bernhard; J. Am. Chem. Soc.; 1948; 70(10); 3426-3428. First Page
