Tetrahydropyran

Description

Tetrahydropyran (THP) is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. It is named by reference to pyran, which contains two double bonds, and may be produced from it by adding four hydrogens. Tetrahydropyran can be used as a solvent in various classical organic reactions such as radical reactions, palladium-catalyzed coupling, and Grignard reactions.

Chemical properties

colorless to light yellow liquid

The Uses of Tetrahydropyran

Tetrahydropyran is is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuff. They are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization.

Definition

ChEBI: Oxane is a saturated organic heteromonocyclic parent that is cyclohexane in which one of the carbon atoms has been replaced by an oxygen atom. It is a saturated organic heteromonocyclic parent and a member of oxanes.

Synthesis

The preparation method of tetrahydropyran involves controlled hydrogenation of alkoxydihydrofurans or alkoxytetrahydrofurans using palladium catalysts and specific temperature and pressure conditions to yield tetrahydropyran compounds efficiently.

Purification Methods

Dry oxane with CaH2, then pass it through a column of silica gel to remove olefinic impurities and fractionally distil it. Free it from peroxides and moisture by refluxing with sodium, then distil it from LiAlH4. Alternatively, peroxides can be removed by treatment with aqueous ferrous sulfate and sodium bisulfate, followed by solid KOH, and fractional distillation from sodium. [Beilstein 17 H 12, 17 I 6, 17 II 18, 17 III/IV 51, 17/1 V 64.]