1927-63-5

Usage

InChI:InChI=1/C11H22O2/c1-2-3-4-6-9-12-11-8-5-7-10-13-11/h11H,2-10H2,1H3

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 111-27-3 hexan-1-ol 
• 33803-59-7 7-<(Tetrahydro-2H-pyran-2-yl)oxy>heptanenitrile 
• 111-25-1 1-bromo-hexane 
• 65785-44-6 6-iodohexanol, tetrahydropyranyl ether 
• 629-11-8 1,6-hexanediol 
• 4286-55-9 1-bromo-6-hexanol 
• 17976-80-6 7-hydroxyheptanenitrile 
• 69161-61-1 2-(prop-2-en-1-yloxy)oxane 
• 4676-84-0 tetrahydropyran-2-yl hydroperoxide 
• 3761-92-0 n-hexylmagnesium bromide 

Downstream Products

• 142-92-7 1-hexyl acetate 
• 53963-10-3 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran 
• 111-27-3 hexan-1-ol 
• 6581-66-4 2-methoxytetrahydropyran 
• 66-25-1 hexanal 
• 152928-72-8 (4R,5S,6S,7R)-4,7-Dibenzyl-5,6-dihydroxy-1,3-bis-(6-hydroxy-hexyl)-[1,3]diazepan-2-one 
• 167824-57-9 (4R,5S,6S,7R)-4,7-Dibenzyl-5,6-dihydroxy-1-(6-hydroxy-hexyl)-3-naphthalen-2-ylmethyl-[1,3]diazepan-2-one 

Relevant academic research and scientific papers

Hierarchical Beta zeolites obtained in concentrated reaction mixtures as catalysts in tetrahydropyranylation of alcohols

Hierarchical zeolites consisting of Beta nanoparticles (15–40 nm) were obtained via hydrothermal treatment of a concentrated zeolite gel-precursor (H2O/Si = 2.5–14) without utilization of complex SDAs. The proposed approach is based on the formation of a large number of zeolite nuclei under particular crystallization conditions, followed by their agglomeration resulting in the dense packing of the particles preventing their further growth. The micelles of cetyltrimethylammonium bromide (CTAB) can be used to additionally limit the growth of zeolite nanoparticles during hydrothermal treatment of concentrated reaction mixtures. Such deceleration of crystallization promotes the formation of highly porous X-ray amorphous nanosized aluminosilicate. Due to the developed mesoporosity and increased accessibility to the acid sites for the molecules of a large size, hierarchical Beta zeolites obtained in the presence of CTAB demonstrate high catalytic activity in the reaction of bulky alcohols (1-octadecanol and 1-adamantanemethanol) with 3,4-dihydro-2H-pyran.

Breaking Structural Energy Constraints: Hydrothermal Crystallization of High-Silica Germanosilicates by a Building-Unit Self-Growth Approach

Zeolites, a class of crystalline microporous materials, have a wide range of practical applications, in particular serving as key catalysts in petrochemical and fine-chemical processes. Millions of zeolite topologies are theoretically possible. However, to date, only 235 frameworks with various tetrahedral element compositions have been discovered in nature or artificially synthesized, among which approximately 50 topologies are available in pure-silica forms. Germanosilicates are becoming an important zeolite family, with a rapidly increasing number of topological structures having unusual double four-membered ring (D4R) building units and large-pore or extra-large-pore systems. The synthesis of their high-silica analogues with higher (hydro)thermal stability remains a great challenge, because the formation of siliceous D4R units is kinetically and thermodynamically unfavorable in hydrothermal systems. Herein, it is demonstrated that such D4R-containing high-silica zeolites with unexpected crystalline topologies (ECNU-24-RC and IM-20-RC) are readily constructed by a versatile route. This strategy provides new opportunities for the synthesis of high-silica zeolite catalysts that are hardly obtainable by conventional hydrothermal synthesis and may also facilitate a breakthrough in increasing the number and types of zeolite materials with practical applications.

Post-synthesis incorporation of Al into germanosilicate ITH zeolites: The influence of treatment conditions on the acidic properties and catalytic behavior in tetrahydropyranylation

Post-synthesis alumination of germanosilicate medium-pore ITH zeolites was shown to be an effective procedure for tuning their acidity. Treatment of ITH zeolites synthesized with different chemical compositions (i.e. Si/Ge = 2.5, 4.4 and 5.8) with aqueous Al(NO3)3 solution led to the formation of strong Br?nsted and Lewis acid sites and an increasing fraction of ultramicro- and meso-pores in Ge-rich ITH samples (Si/Ge = 2.5 and 4.4). The concentration of Al incorporated into the framework increases with decreasing Si/Ge ratio of the parent ITH. The increasing temperature of alumination from 80 to 175 °C (HT conditions) resulted in (1) a 1.5-2-fold increase in the concentration of Br?nsted acid sites formed and (2) a decreasing fraction of framework Al atoms detectable with base probe molecules (i.e. pyridine, 2,6-di-tert-butylpyridine), i.e. an increased concentration of the "inner" acid sites. The activity of prepared Al-substituted ITH zeolites in tetrahydropyranylation of alcohols is enhanced with increasing amount of accessible acid sites in bulky crystals (e.g. alumination at lower temperature) or with increasing total concentration of acid centres within tiny ITH crystals (e.g. alumination under HT conditions). This trend became more prominent with increasing kinetic diameter of the substrate molecules under investigation (methanol 1-propanol 1-hexanol).

Sulfonic acid-functionalized LUS-1: an efficient catalyst for tetrahydropyranylation/depyranylation of alcohols

Efficient acidic functionalization of mesoporous silica LUS-1 (Laval University Silica) and its application as a recyclable heterogeneous catalyst for DHP (3,4-dihydro-2H-pyran) protection of alcohols and the subsequent removal of the corresponding protecting group have been reported. This green method offers a number of advantages such as short reaction time, good yields of protection and deprotection, simple work-up procedure, recyclable catalyst, and environmentally friendly conditions.

Synthesis of Ethers via Reaction of Carbanions and Monoperoxyacetals

Although transfer of electrophilic alkoxyl ("RO+") from organic peroxides to organometallics offers a complement to traditional methods for etherification, application has been limited by constraints associated with peroxide reactivity and stability. We now demonstrate that readily prepared tetrahydropyranyl monoperoxyacetals react with sp3 and sp2 organolithium and organomagnesium reagents to furnish moderate to high yields of ethers. The method is successfully applied to the synthesis of alkyl, alkenyl, aryl, heteroaryl, and cyclopropyl ethers, mixed O,O-acetals, and S,S,O-orthoesters. In contrast to reactions of dialkyl and alkyl/silyl peroxides, the displacements of monoperoxyacetals provide no evidence for alkoxy radical intermediates. At the same time, the high yields observed for transfer of primary, secondary, or tertiary alkoxides, the latter involving attack on neopentyl oxygen, are inconsistent with an SN2 mechanism. Theoretical studies suggest a mechanism involving Lewis acid promoted insertion of organometallics into the O-O bond.

Tetrahydropyranylation of alcohols and phenols using polystyrene supported lewis acids as catalysts

Polystyrene supported TiCl4 (Ps-TiCl4) and polystyrene supported FeCl3(Ps-FeCl3) were prepared by coordinating Lewis acids with polystyrene. The catalysts were characterized by TGA, BET, SEM, IR and pyridine-adsorbed IR. The loading of Ps-TiCl4 and Ps-FeCl3 were 0.35 and 0.3 mmol·g-1 respectively. Both catalysts were found to be efficient for the tetrahydropyranylation and detetrahydropyranylation of various alcohols and phenols in different solvents. Two catalysts can be recovered and reused for five times with good activity. Polystyrene supported TiCl4 (Ps-TiCl4) and polystyrene supported FeCl3(Ps-FeCl 3) were prepared by coordinating Lewis acids with polystyrene. The catalysts were characterized by TGA, BET, SEM, IR and pyridine-adsorbed IR. The loading of Ps-TiCl4 and Ps-FeCl3 were 0.35 and 0.3 mmol·g-1 respectively. Both catalysts were found to be efficient for the tetrahydropyranylation and detetrahydropyranylation of various alcohols and phenols in different solvents. Two catalysts can be recovered and reused for five times with good activity. Copyright

1,6-Hexanediamine methanesulfonate: A mild and efficient catalyst for the tetrahydropyranylation of alcohols under solvent-free conditions

Various alcohols react with 3,4-dihydro-2 H-pyran under mild conditions using a catalytic amount of 1,6-hexanediamine methanesulfonate. It affords the corresponding tetrahydropyranyl ethers in good yields at a faster rate in the absence of solvent. Taylor & Francis Group, LLC.

Tetrahydropyranylation of alcohols over modified zeolites

A catalytic amount of Moβ enables tetrahydropyranylation of various alcohols, phenols and naphthols under mild reaction conditions at room temperature in moderate to excellent yields within short reaction times is presented. The catalyst Moβ is reused without significant loss of activity. The product isolation is simple and environmentally benign.

Allyl tetrahydropyranyl ether: a versatile alcohol/thiol protecting reagent

Allyl tetrahydropyranyl ether (ATHPE) can be used as a versatile protecting reagent. In combination with NBS/I2, O-allyl group can easily be replaced by hydroxyls (including tertiary-OH) or thiols, in the molecules comprising other reactive fun

Carbon tetrabromide/sodium triphenylphosphine-m-sulfonate (TPPMS) as an efficient and easily recoverable catalyst for acetalization and tetrahydropyranylation reactions

A solid complex, conveniently prepared from carbon tetrabromide and sodium triphenylphos-phine-m-sulfonate (TPPMS), can be used as an easily recoverable catalyst for the selective acetalization of aldehydes and tetrahydropyranylation of alcohols. The catalyst can be recovered by simple pre-cipitation with ether and can be reused at least 7 times without loss of catalytic activity.