Meldrum's acid
From Wikipedia, the free encyclopedia
| Meldrum's Acid | |
|---|---|
 |
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| IUPAC name | 2,2-Dimethyl-1,3-dioxane-4,6-dione |
| Identifiers | |
| CAS number | [2033-24-1] |
| SMILES | O=C(C1)OC(C)(C)OC1=O |
| InChI | 1/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3 |
| InChI key | GXHFUVWIGNLZSC-UHFFFAOYAM |
| Properties | |
| Molecular formula | C6H8O4 |
| Molar mass | 144.1253 g/mol |
| Density | ? g/cm3 |
| Melting point |
94-96 °C |
| Boiling point |
°C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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] References
- ^ Meldrum, A. N. J. Chem. Soc. 1908, 93, 598.
- ^ The Structure of Meldrum's Supposed beta-Lactonic Acid David Davidson, Sidney A. Bernhard; J. Am. Chem. Soc.; 1948; 70(10); 3426-3428. doi:10.1021/ja01190a060
[edit] External links
- Synlett Spotlight Website
- Meldrum's acid in Organic Syntheses Website
| International Chemical Identifier | |
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| InChI= | 1/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3 |
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