Choline chloride based deep eutectic solvent as an efficient solvent for the benzylation of phenols

Singh, Abhilash S.; Shendage, Suresh S.; Nagarkar, Jayashree M.

doi:10.1016/j.tetlet.2014.11.053

Cited by 21 publications

(14 citation statements)

References 40 publications

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“…[95] The DES was recovered by addition of water and extraction with ethyl acetate, followed by drying at 80 ºC, its reusability being tested for five consecutive cycles with a certain decrease in the yield after the fourth cycle.…”

Section: Scheme 25 Alkylation Reactions Of Anilines and Phenolsmentioning

confidence: 99%

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

et al. 2016

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This microreview summarizes the use of deep eutectic solvents (DES) and related melts in Organic Synthesis. This type of solvents combine the great advantages of other proposed environmentally benign alternative solvents, such as low toxicity, high availability, low inflammability, high recyclability, low volatility and low price, avoiding many disadvantages of these neoteric media. The fact that many of the components of the mixture come directly from Nature assures their biodegradability and renewability. The classification and distribution of the reactions in different sections along this microreview, as well as the emphasis paid to their scope, easily allows a general reader to understand the actual state of art, and the great opportunities opened, not only for academic proposes but also for industry.

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Section: Scheme 25 Alkylation Reactions Of Anilines and Phenolsmentioning

confidence: 99%

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

et al. 2016

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“…124 It was found that ChCl/urea was promising solvent and phase-transfer-medium for benzylation of phenols. 124 It was found that ChCl/urea was promising solvent and phase-transfer-medium for benzylation of phenols.…”

Section: Scheme 67mentioning

confidence: 99%

Recent advances in the application of deep eutectic solvents as sustainable media as well as catalysts in organic reactions

et al. 2015

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Deep eutectic solvents (DESs), also known as deep eutectic ionic liquids (DEILs) or low-melting mixtures (LMMs) or low transition temperature mixtures (LTTMs) in the literature, have become more and more attractive in recent years due to their interesting properties and benefits, such as low cost of components, easy to prepare, tunable physicochemical properties, negligible vapor pressure, non-toxicity, biorenewability and biodegradability. These eutectic mixtures have been widely used as green and sustainable media as well as catalysts in many chemical processes. This review focuses on recent advances using DESs in organic reactions including addition reactions, cyclization reactions, replacement reactions, multicomponent reactions, condensation reactions, oxidation reactions, and reducing reactions.

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“…In addition to the traditional methodologies, Maki's group reported the benzylation of the hydroxyl group of phenol in the presence of Hünig's base (N,N-diisopropylethylamine) without the use of solvent. 6 Recently, phase-transfer-catalyst ( tbutyl ammonium bromide)-mediated benzylation of phenols with an inorganic base in water was successfully achieved by Wu et al 7 More eco-friendly media, room-temperature ionic liquids (RTILs), were also used for the benzylation of phenols by Nagarkar et al 8 In their study, benzylation using choline chloride (ChCl)-based task-forced DES (deep eutectic solvent), which consisted of ChCl, urea, and KOH, was achieved. It is of interest that choline hydroxide, a basic IL, has attracted much attentions in synthetic chemistry due to its unique properties.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, phase‐transfer‐catalyst ( t ‐ butyl ammonium bromide)‐mediated benzylation of phenols with an inorganic base in water was successfully achieved by Wu et al 7 . More eco‐friendly media, room‐temperature ionic liquids (RTILs), were also used for the benzylation of phenols by Nagarkar et al 8 . In their study, benzylation using choline chloride (ChCl)‐based task‐forced DES (deep eutectic solvent), which consisted of ChCl, urea, and KOH, was achieved.…”

Section: Introductionmentioning

confidence: 99%

Choline Hydroxide as a Versatile Medium for Catalyst‐Free O‐Functionalization of Phenols

Kwon

Joo

Park

et al. 2020

Bulletin Korean Chem Soc

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A versatile synthetic protocol for benzyl phenyl ether preparation via O-alkylation of phenolic oxygen with readily available benzyl derivatives was demonstrated. The newly designed procedure was carried out using an eco-friendly medium, room-temperature ionic liquid (choline hydroxide), under metal-and base-catalyst-free aerobic conditions. The reaction platform was also successfully applied to phenol protection strategy.

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Choline chloride based deep eutectic solvent as an efficient solvent for the benzylation of phenols

Cited by 21 publications

References 40 publications

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

Recent advances in the application of deep eutectic solvents as sustainable media as well as catalysts in organic reactions

Choline Hydroxide as a Versatile Medium for Catalyst‐Free O‐Functionalization of Phenols

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