Solketal

Solketal
IUPAC name (2,2-dimethyl-1,3-dioxolan-4-yl)methanol
Other names Isopropylidene glycerol
Identifiers
CAS number	100-79-8 Y
PubChem	7528
ChemSpider	7247 Y
Jmol-3D images	Image 1
SMILES CC1(OCC(O1)CO)C
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
Properties
Molecular formula	C6H12O3
Molar mass	132.15768
Boiling point	188-189 ºC
Solubility in water	Miscible
Hazards
Flash point	80 ºC
Y (verify) (what is: Y/N?) 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 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 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

"Solketal". Logo of chemBlink Inc. Online Database of Chemicals from Around the World. Archived from the original on 31 October 2010. 

Tetrahedron, 52, p. 9387, 1996