Solketal

Solketal

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Names
IUPAC name (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol
Other names Isopropylidene glycerol
Identifiers
CAS Number	100-79-8 Y
ChemSpider	7247 Y
Jmol 3D model	Interactive image
PubChem	7528
InChI InChI=1S/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3 Y Key: RNVYQYLELCKWAN-UHFFFAOYSA-N Y InChI=1/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3 Key: RNVYQYLELCKWAN-UHFFFAOYAB
SMILES CC1(OCC(O1)CO)C
Properties
Chemical formula	C6H12O3
Molar mass	132.16 g·mol−1
Boiling point	188 to 189 °C (370 to 372 °F; 461 to 462 K)
Solubility in water	Miscible
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Solketal is a protected form of glycerol with an isopropylidene acetal group joining 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 groups 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

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