Solketal

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.

Solketal

Names
IUPAC name (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol
Other names Isopropylidene glycerol
Identifiers
CAS Number	100-79-8 Racemic 14347-78-5 R enantiomer 22323-82-6 S enantiomer
3D model (JSmol)	Interactive image
ChemSpider	7247
ECHA InfoCard	100.002.626
PubChem CID	7528
UNII	3XK098O8ZW
CompTox Dashboard (EPA)	DTXSID9021845
InChI InChI=1S/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3 Key: RNVYQYLELCKWAN-UHFFFAOYSA-N InChI=1/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3 Key: RNVYQYLELCKWAN-UHFFFAOYAB
SMILES OCC1COC(C)(C)O1
Properties
Chemical formula	C6H12O3
Molar mass	132.159 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)
Solubility in water	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).
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Infobox references

References

• Mary Renoll and Melvin S. Newman (1955). "dl-ISOPROPYLIDENEGLYCEROL". Organic Syntheses. 28: 73.; Collective Volume, 3, p. 502
• Sanderson, John R.; Lin, Jiang J.; Duranleau, Roger G.; Yeakey, Ernest L.; Marquis, Edward T. (1988). "Free radicals in organic synthesis. A novel synthesis of glycerol based on ethylene glycol and formaldehyde". Journal of Organic Chemistry. 53 (12): 2859. doi:10.1021/jo00247a043.
• "Solketal". Logo of chemBlink Inc. Online Database of Chemicals from Around the World. Archived from the original on 31 October 2010.
• Matsumoto, Yoshihiko; Mita, Keisuke; Hashimoto, Keiji; Iio, Hideo; Tokoroyama, Takashi (1996). "Selective cleavage of ethers using silica-alumina gel catalysts prepared by the sol-gel method". Tetrahedron. 52 (28): 9387. doi:10.1016/0040-4020(96)00501-7.