32996-90-0

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 95-48-7 ortho-cresol 
• 108-95-2 phenol 
• 4203-50-3 2-phenoxytetrahydropyran 

Downstream Products

• 148344-52-9 2-bromomethyl-1-(2'-tetrahydropyranyloxy)benzene 
• 189574-84-3 (E)-ethyl 3-(2-hydroxy-3-methylphenyl)acrylate 
• 259209-22-8 2-hydroxy-3-methylphenyl boronic acid 
• 95-48-7 ortho-cresol 

Relevant academic research and scientific papers

Elaborate Tuning in Ligand Makes a Big Difference in Catalytic Performance: Bulky Nickel Catalysts for (Co)polymerization of Ethylene with Promising Vinyl Polar Monomers

To reveal effect of electronic or steric modification of phosphino-phenolate nickel complex for preparing optimized catalysts, we take elaborated studies on structure-performance relationship by finely modifying substituents on ortho-phenoxy position or phosphorus moiety of this catalyst. It reveals that these newly synthesized complexes are thermally robust, and exhibits very high activity (up to 107 g molNi?1 h?1) in ethylene polymerization even at 120 °C. Associated with stoichiometric experiments, experimental results prove that nickel complexes bearing electron-withdrawing substituents on ortho-phenoxy position or electron-donating substituents on phosphorus atom show higher activity than contrastive catalysts toward ethylene polymerization and ethylene–methyl acrylate (MA) copolymerization. Among these catalysts, 3 g bearing a strong electron-withdrawing substituent on ortho-phenoxy position exhibits the highest activity, and produces copolymers with the highest molecular weight and analogous MA incorporation. Various challenging polar vinyl monomers, like polyethylene glycol monomethyl ether acrylate, can be efficiently copolymerized with ethylene.

Short communication: Catalytic tetrahydropyranylation of phenols and alcohols using vanadium(V)-substituted polyoxomolybdates

Alcohols and phenols were tetrahydropyranylated in the presence of H 7[PMo8V4O40] in good to excellent yields in acetonitrile and under solventfree reaction conditions. A mild and convenient method for the formation and deprotection of ethers (THP ethers) is described. The formation of THP ethers from the corresponding alcohols was accomplished in the presence of acid-sensitive functional groups.

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.

Efficient and convenient procedure for protection of hydroxyl groups to the THP, THF and TMS ethers and oxidation of these ethers to their aldehydes or ketones in [BPy]FeCl4 as a low cost room temperature ionic liquid

Alcohols were converted to the corresponding THP, THF or TMS ethers in high to excellent yields in 1-n-butylpyridinium chloroferrate media as a stable and low cost room temperature ionic liquid. In addition, oxidation of these ethers to their aldehydes or ketones without any overoxidation reactions in this ionic liquid was also performed.

Microwave-assisted preparation of imidazolium-based tetrachloroindate(III) and their application in the tetrahydropyranylation of alcohols

Microwave-assisted preparation of 1-alkyl-3-methylimidazolium tetrachloroindate(III), [Rmim][InCl4] (R = methyl, ethyl, butyl, hexyl, octyl) and their application as recyclable catalysts for the efficient and eco-friendly protection of alcohols to form tetrahydropyranyl (THP) ethers are described.

Spanish sepiolite clay as a new heterogeneous catalyst for the tetrahydropyranylation of alcohols and phenols

OH-protection of alcohols and phenols by heating the hydroxylated compound with 3,4-dihydro-2H-pyrane in the presence of a readily available and inexpensive spanish sepiolite heterogeneous acid clay catalyst is described. Isolated yields, not optimized, were in the range 29-99%.

One Pot Synthesis of Polycyclic Oxygen Aromatics. Part IV. Reaction of THP Ether of 2-Bromomethyl Phenols

Reaction of 2-bromomethyl-1-(2'-tetrahydropyranyloxy)benzene 3a with tetrachlorocatechol (TCC) in acetone in presence of anhydrous K2CO3 resulted in the formation of diastereomeric products to which cis- and trans- 6-chloro-8-hydroxy-8-(2-oxopropyl)spiroxanthen-9,2'(1'H)benzofuran>-7(8H)-one (7a and 8a) structures were assigned, along with tetrachlorocatechol ethers (5a and 6a).Similar reaction of 3a with tetrabromocatechol (TBC) gave the expected monobromo compounds 7d and 8d along with the ethers 5d and 6d.When the reaction was repeated with substrates 3b-c with TCC/TBC in ketonic solvents (acetone/methyl ethyl ketone), the corresponding compounds 5b-c to 8b-c, 5e-f to 6e-f, 7e-g and 8e-h were obtained.A suitable explanation has been given for the formation of acetonyl compound 6 in this reaction.

AlPO4 and AlPO4-Al2O3 as new heterogeneous catalysts for the solvent-free tetrahydropyranylation of alcohols and phenols

OH-protection of alcohols and phenols by heating the hydroxylated compound with 3,4-dihydro-2H-pyrane in the presence of an AlPO4 or AlPO4-Al2O3 heterogeneous acid catalyst is described. Isolated yields, not optimized, were in the range 50-99%.

The Thermal ortho-Substitution of Phenols by Vinyl Ethers

Pyrolysis of a mixture of phenol and 3,4-dihydro-2H-pyran (6) at 150-180 deg C resulted in the formation of 2-(tetrahydro-2H-pyran-2-yl)phenol (3a) in moderate yield.This selective ortho-substitution reaction has been investigated for a range of phenols and a number of vinyl ethers.While it was found to be a fairly general reaction for phenols, only with the vinyl ether (6) and 2,3-dihydrofuran (28a) was the reaction found to be regioselective.Aluminium phenylate strongly catalyses the reaction of phenol with (6), which proceeded under these conditions at room temperature.An ene-type mechanism is proposed for the reaction.