Solketal
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| Solketal | |
|---|---|
| File:Solketal.png | |
| (2,2-dimethyl-1,3-dioxolan-4-yl)methanol | |
| Other names Isopropylidene glycerol | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 100-79-8 |
| PubChem | 7528 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C6H12O3 |
| Molar mass | 132.15768 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Solketal is a protected form of glycerol with an isopropylidene group bound to two neighboring hydroxyl groups. Solketal contains a chiral center on the center carbon of the glycerol backbone, and so can be purchased as either the racemate or as one of the two enantiomers. Solketal has been used extensively in the synthesis of mono-, di- and triglycerides by ester bond formation. The free hydroxyl groupd of solketal can be esterified with a carboxylic acid to form the protected monoglyceride, where the isopropylene group can then be removed using an acid catalyst in aqueous or alcoholic medium. The unprotected diol can then be esterified further to form either the di- or triglyceride.
References
Organic Syntheses, Coll. Vol. 3, p. 502, 1955
The Journal of Organic Chemistry, 53, p. 2859, 1988
Tetrahedron, 52, p. 9387, 1996
