Ferrous methanesulfonate as an efficient and recyclable catalyst for the tetrahydropyranylation of alcohols and phenols under solvent-free conditions

doi:10.1039/C1RA00591J

Paper

Ferrous methanesulfonate as an efficient and recyclable catalyst for the tetrahydropyranylation of alcohols and phenols under solvent-free conditions

Published Nov 28, 2011 · Min Wang, Zhiguo. Song, Xin Wan

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Abstract

Ferrous methanesulfonate catalyzed tetrahydropyranylation of alcohols (benzylic, primary, isomerical, tertiary, cyclic, allyl, and furyl) and phenols at room temperature under solvent-free conditions has been developed. The catalytic activity of sixteen metal methanesulfonates was compared under the same conditions, ferrous methanesulfonate proved to be the best. It can be recovered easily and reused for several times without distinct deterioration in catalytic activity. During the competitive protection of the hydroxyl groups between an alcohol and a phenol, tetrahydropyranyl ether formed exclusively with the alcohol. A possible catalytic mechanism was proposed.

Study Snapshot

Ferrous methanesulfonate is an efficient and recyclable catalyst for tetrahydropyranylation of alcohols and phenols under solvent-free conditions, with potential applications in organic synthesis.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Ferrous methanesulfonate as an efficient and recyclable catalyst for the tetrahydropyranylation of alcohols and phenols under solvent-free conditions

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References

Gal3 catalyzed tetrahydropyranylation of alcohols and phenols

Gal3 catalyzes the tetrahydropyranylation of alcohols and phenols in dichloromethane, providing good to excellent yields in the synthesis of tetrahydropyranyl acetals.

Ferrous methanesulfonate as an efficient and recyclable catalyst for chemoselective synthesis of 1,1-diacetate from aldehydes

Ferrous methanesulfonate is an efficient and recyclable catalyst for chemoselective synthesis of 1,1-diacetate from aldehydes, with its catalytic activity remaining stable for several reuses.

Three-Component Mannich Reaction of Aromatic Ketones, Aldehydes and Amines Catalyzed by Reusable Aluminium Methanesulfonate

The study presents a reusable aluminium methanesulfonate-catalyzed three-component Mannich reaction for the efficient synthesis of -aminocarbonyl compounds from aromatic ketones, aldehydes, and amines.

Thermal decomposition of metal methanesulfonates in air

Thermal decomposition of metal methanesulfonates in air produces metal oxides for transition metals and sulphates for alkali rare metals, with pyrolysis products varying between metals and mixtures of sulphate and oxide.

Efficient and green tetrahydropyranylation and deprotection of alcohols and phenols by using activated carbon supported sulfuric acid

Using activated carbon supported sulfuric acid, this study presents a green and efficient method for DHP protection of alcohols and phenols and their subsequent removal.

Praseodymium Methanesulfonate Catalyzed One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2‐(1H)‐ones

Praseodymium methanesulfonate catalyst efficiently synthesizes 3,4-dihydropyrimidin2(1H)ones in one-pot in absolute ethanol, with easy recovery and reuse.

Regioselective tetrahydropyranylation of alcohols catalyzed by Fe(HSO4)3

Fe(HSO4)3 catalyzes selective tetrahydropyranylation of alcohols, efficiently protecting them as their tetrahydropranyl ethers in good to high yields under mild, heterogeneous reaction conditions.

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