Solketal

Solketal
Names
IUPAC name
(2,2-Dimethyl-1,3-dioxolan-4-yl)methanol
Other names
Isopropylidene glycerol
Identifiers
100-79-8 Racemic YesY
14347-78-5 R enantiomer N
22323-82-6 S enantiomer N
3D model (Jmol) Interactive image
ChemSpider 7247 YesY
ECHA InfoCard 100.002.626
PubChem 7528
UNII 3XK098O8ZW N
Properties
C6H12O3
Molar mass 132.16 g·mol−1
Appearance clear colorless liquid
Density 1.063 g/mL at 25 °C
Boiling point 188 to 189 °C (370 to 372 °F; 461 to 462 K)
Miscible
Solubility Miscible in most organic solvents (alcohols, ethers, hydrocarbons)
Hazards
Flash point 80 °C (176 °F; 353 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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

This article is issued from Wikipedia - version of the 9/7/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.