1,3-dioxolane
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IUPAC name
Dioxolane
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| Other names
1,3-dioxolane, formal glycol
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3D model (JSmol)
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| ECHA InfoCard | 100.010.422 | ||
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PubChem CID
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| Properties | |||
| C3H6O2 | |||
| Molar mass | 74.08 g/mol | ||
| Density | 1.06 g/cm3 | ||
| Melting point | −95 °C (−139 °F; 178 K) | ||
| Boiling point | 75 °C (167 °F; 348 K) | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dioxolane is a heterocyclic acetal with the chemical formula (CH2)2O2CH2. It is related to tetrahydrofuran by interchange of one oxygen for a CH2 group. The corresponding saturated 6-membered C4O2 rings are called dioxanes. The isomeric 1,2-dioxolane (wherein the two oxygen centers are adjacent) is a peroxide. 1,3-Dioxolane is used as a solvent and as a comonomer in polyacetals.
Dioxolanes are a group of organic compounds containing the dioxolane ring. Dioxolanes can be prepared by acetalization of aldehydes and ketalization of ketones with ethylene glycol.
(+)-cis-Dioxolane is the trivial name for L-(+)-cis-2-methyl-4-trimethylammoniummethyl-1,3-dioxolane iodide which is a muscarinic acetylcholine receptor agonist.
Organic compounds containing carbonyl groups sometimes need protection so that they do not undergo reactions during transformations of other functional groups that may be present. A variety of approaches to protection and deprotection of carbonyls including as dioxolanes are known. For example, consider the compound methyl cyclohexanone-4-carboxylate, where lithium aluminium hydride reduction will produce 4-hydroxymethylcyclohexanol. The ester functional group can be reduced without affecting the ketone by protecting the ketone as a ketal. The ketal is produced by acid catalysed reaction with ethylene glycol, the reduction reaction carried out, and the protecting group removed by hydrolysis to produce 4-hydroxmethylcyclohexanone.
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