3,4-Dihydropyran

3,4-Dihydropyran (DHP) is a heterocyclic compound with the formula C5H8O. The six-membered C5O ring has the unsaturation adjacent to oxygen. The isomeric 3,6-dihydropyran has a methylene separating the double bond and oxygen. DHP is used for protecting group for alcohols. It is a colorless liquid.

Preparation
Dihydropyran is prepared by the dehydration of tetrahydrofurfuryl alcohol over alumina at 300–400 °C. THFA is itself prepared from tetrahydro-2-furoic acid.
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Reactions
In organic synthesis, the 2-tetrahydropyranyl (THP) group is used as a protecting group for alcohols. Reaction of the alcohol with DHP forms a THP ether, protecting the alcohol from a variety of reactions. The alcohol can later be restored by acidic hydrolysis, concomitant with formation of 5-hydroxypentanal.


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