82065-19-8

Basic information

• Product Name: 2-Phenyltetrahydro-2H-pyran-4-ol
• Synonyms: 2-Phenyltetrahydro-2H-pyran-4-ol;cis-2-Phenyltetrahydro-2H-pyran-4-ol;(2R,4S)-2-phenyloxan-4-ol
• CAS NO: 82065-19-8
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.22766
• Mol File: 82065-19-8.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Phenyltetrahydro-2H-pyran-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenyltetrahydro-2H-pyran-4-ol(82065-19-8)
• EPA Substance Registry System: 2-Phenyltetrahydro-2H-pyran-4-ol(82065-19-8)

Safety Data

• Hazardous Substances Data: 82065-19-8(Hazardous Substances Data)

Upstream product

• 627-27-0 homoalylic alcohol 
• 100-52-7 benzaldehyde 
• 2397-79-7 2-phenyl-4H-pyran-4-one 
• 64-17-5 ethanol 
• 94426-72-9 2-(2-(benzyloxy)ethyl)oxirane 
• 132148-94-8 1-Phenyl-5-tributylstannanyl-pentane-1,3-diol 
• 546-67-8 lead(IV) tetraacetate 

Downstream Products

• 82110-16-5 (2R,4S)-2-phenyltetrahydro-2H-pyran-4-ol 
• 82110-28-9 (S)-2-phenyl-tetrahydropyran-4-one 
• 82110-27-8 (R)-2-phenyl-tetrahydro-pyran-4-one 
• 1190840-60-8 (2S,4R)-1-[1-(2-phenyl-tetrahydro-pyran-4-yl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one 
• 1190840-52-8 1-[1-(2-phenyl-tetrahydro-pyran-4-yl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one 
• 147688-62-8 (+/-)-2-phenyl-tetrahydro-2H-pyran-4-one 
• 1359858-75-5 C₁₂H₁₃NO 
• 1359858-76-6 C₁₂H₁₄O₃ 
• 1412450-94-2 C₂₁H₂₄N₂O₃S 

Relevant articles and documents

Diastereoselective synthesis of 2,4-disubstituted tetrahydropyranols and ethers via a prins-type cyclization catalyzed by scandium triflate

The reaction of aldehydes with homoallylic alcohols catalyzed by scandium triflate gives rise to the formation of 2-substituted tetrahydropyran-4-ols and ethers in good overall yields and with 'all-cis' configurations and high diastereoselectivities. The

Scandium triflate catalyzed in situ Prins-type cyclization: Formations of 4-tetrahydropyranols and ethers

The reaction of aldehydes with homoallyl alcohols catalyzed by scandium triflate generates tetrahydropyran-4-ol and ethers in good yields.

Investigation of Prins reaction for the synthesis of 2, 4-disubstituted tetrahydropyran derivatives and 1, 3-dioxanes using polyaniline supported acid as reusable catalyst

The Prins cyclization of homoallyl alcohol with a variety of aldehydes were observed under reflux condition in dichloromethane using both polyaniline supported TsOH (PANI-TsOH) and FeCl3 (PANI- FeCl3) as reusable acid catalysts with the formation of 2,4-disubstituted tetrahydropyran ether as single product. In case of 4-, 3- and 2- nitro benzaldehydes, the reaction generated acetal of the aldehyde and homoallylic alcohol as single product. Additionally, both catalysts were investigated for the synthesis of 1, 3-dioxane in dichloromethane under reflux and at ambient temperature Indian Academy of Sciences.

The 'aqueous' Prins cyclization: A diastereoselective synthesis of 4-hydroxytetrahydropyran derivatives

Phosphomolybdic acid (H3PMo12O40, a heteropoly acid) is found to catalyze efficiently the Prins cyclization of homoallylic alcohols with aldehydes in water at room temperature to provide tetrahydropyran-4-ol derivatives in high yields with all cis-selectivity. Only cyclic ketones can give spirocyclic products. The use of phosphomolybdic acid in water makes this procedure simple, more convenient, cost-effective, and environmentally friendly. Georg Thieme Verlag Stuttgart.