1927-62-4

Basic information

• Product Name: 2-BENZYLOXYTETRAHYDROPYRAN
• Synonyms: 2-BENZYLOXYTETRAHYDROPYRAN;(Tetrahydro-2H-pyran-2-yl)benzyl ether;2-Benzyloxy-3,4,5,6-tetrahydro-2H-pyran;2-Benzyloxytetrahydro-2H-pyran;Benzyl(tetrahydro-2H-pyran)-2-yl ether;Benzyl(tetrahydro-2H-pyran-2-yl) ether;Tetrahydro-2H-pyran-2-yl(benzyl) ether
• CAS NO: 1927-62-4
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25
• EINECS: 200-456-8
• Product Categories: API intermediates;Building Blocks;Heterocyclic Building Blocks;Pyrans
• Mol File: 1927-62-4.mol
• Article Data: 113

Chemical Properties

• Boiling Point: 65 °C0.1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.048 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00507mmHg at 25°C
• Refractive Index: n20/D 1.5138(lit.)
• CAS DataBase Reference: 2-BENZYLOXYTETRAHYDROPYRAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BENZYLOXYTETRAHYDROPYRAN(1927-62-4)
• EPA Substance Registry System: 2-BENZYLOXYTETRAHYDROPYRAN(1927-62-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1927-62-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 22, p. 2335, 1992 DOI: 10.1080/00397919208019088

InChI:InChI=1/C12H16O2/c1-2-6-11(7-3-1)10-14-12-8-4-5-9-13-12/h1-3,6-7,12H,4-5,8-10H2

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 100-51-6 benzyl alcohol 
• 96754-03-9 2-(phenylsulfonyl)tetrahydro-2H-pyran 
• 112321-19-4 4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-one 
• 94800-75-6 2-(2,4,6-Trimethyl-phenoxy)-tetrahydro-pyran 
• 873-75-6 4-bromobenzenemethanol 
• 69161-61-1 2-(prop-2-en-1-yloxy)oxane 
• 142-68-7 TETRAHYDROPYRANE 
• 49624-41-1 2-Fluor-tetrahydropyran 
• 1219692-88-2 4-(tetrahydropyran-2'-yloxymethyl)-iodobenzene 
• 14642-79-6 benzyloxy-trimethylsilane 
• 694-54-2 tetrahydro-2H-2-pyranol 
• 35271-56-8 3-(4-nitrophenyl)propyl-2-en-1-ol 
• 619-73-8 4-nitrobenzyl chloride 

Downstream Products

• 59556-69-3 2,3,5-tri-O-benzoyl-1-O-benzyl-β-D-ribofuranose 
• 4132-31-4 benzyl 2,3,4,6-tetra-O-benzyl-β,α-D-glucopyranoside 
• 64042-26-8 tetrahydro-2-(phenylseleno)-2H-Pyran 
• 137469-53-5 5-Benzyloxy-5-phenylselanyl-pentan-1-ol 
• 53172-91-1 (benzyloxy)(tert-butyl)dimethylsilane 
• 6581-66-4 2-methoxytetrahydropyran 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 620-05-3 iodomethylbenzene 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 100-52-7 benzaldehyde 
• 60343-28-4 Benzyl 5-bromovalerate 
• 2159-32-2 4-(benzyloxy)pentan-1-ol 
• 266683-57-2 2-benzyloxy-3-bromotetrahydropyran 

Relevant articles and documents

Phosphorus pentoxide as an efficient catalyst for the tetrahydropyranylation of alcohols under solvent-free conditions

A facile and efficient method for the preparation of tetrahydropyranyl ethers from alcohols is improved in solvent-free media. These reactions are catalyzed by P2O5 and afford various tetrahydropyranyl ethers in shorter reaction time, with good to excellent yields (75-95%) at room temperature. This method is also compatible with substrates containing acid-sensitive functional groups.

2,3-Dichloro-5,6-dicyano-p-benzoquinone as a Mild and Efficient Catalyst for the Tetrahydropyranylation of Alcohols

Hydroxy compounds readily add to 3,4-dihydro-2H-pyran under neutral conditions in the presence of a catalytic amount of 2,3-dichloro-5,6-dicyano-p-benzoquinone, to give high yields of the corresponding tetrahydropyranyl ethers.

Mild and efficient tetrahydropyranylation of alcohols and dehydropyranylation of THP ethers catalyzed by ferric perchlorate

A simple, mild and efficient method for tetrahydropyranylation and dehydropyranylation of alcohols in the presence of ferric perchlorate are described.

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.

Fully recyclable Br?nsted acid catalyst systems

Homogeneous and heterogeneous sulfonic acid catalysts are some of the most common catalysts used in organic chemistry. This work explores an alternative scheme using a fully recyclable polymeric solvent (a poly-α-olefin (PAO)) and soluble PAO-anchored polyisobutylene (PIB)-bound sulfonic acid catalysts. This PAO solvent is nonvolatile and helps to exclude water by its nonpolar nature which in turn drives reactions without the need for distillation of water, avoiding the need for excess reagents. This highly nonpolar solvent system uses polyisobutylene (PIB) bound sulfonic acid catalysts that are phase-anchored in solvents like PAO. The effectivenes of these catalysts was demonstrated by their use in esterifications, acetalizations, and multicomponent condensations. These catalysts and the PAO solvent phase show excellent recyclability in schemes where products are efficiently separated. For example, this non-volatile polymeric solvent and the PIB-bound catalyst can be recycled quantitatively when volatile products are separated and purified by distillation. In other cases, product purification can be effected by product self-separation or by extraction.

Direct Conversion of TMS-ethers to THP-ethers Catalyzed by {[K.18-Crown-6]Br3}n

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