Task-oriented use of ionic liquids: efficient acetylation of alcohols and phenols

López, Ignacio; Bravo, José; Caraballo, Manuel; Barneto, José Luis; Silvero, Guadalupe

doi:10.1016/j.tetlet.2011.04.079

Cited by 23 publications

(9 citation statements)

References 19 publications

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“…Other ChCl-based DESs such as ChCl-malonic acid, ChCl-glycine, ChCl-citric acid and ChCl-urea were also examined. The results clearly show that ChCl-Ox is the optimal solvent and catalyst for the reaction (Table 1, entries [13][14][15][16][17]. It is worth to note that in a blank reaction without a catalyst (entry 18) only trace amounts of the corresponding product were obtained even after prolonged reaction times (2 h).…”

Section: Resultsmentioning

confidence: 82%

“…The acid-catalyzed condensation of dimedone with aromatic aldehydes to get 1,8-dioxo-octahydroxanthenes seems to be a highly efficient reaction [4,15]. It is worthy to mention that, with the addition of malononitrile to the reaction mixture, the preparation of tetrahydrobenzo[b]pyran scaffolds would be possible [16,17]. The conventional synthetic method for the preparation of 4-azaphenanthrene-3,10-diones involves a four-component condensation of Meldrum's acid, an aldehyde, primary amine or ammonium acetate and different 1,3-dicarbonyl compounds under different conditions [8,9].…”

Section: Introductionmentioning

confidence: 99%

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One-pot multi-component process for the synthesis of 4-azaphenanthrene-3,10-dione, 1,8-dioxo-octahydroxanthene and tetrahydrobenzo[b]pyran derivatives catalyzed by the deep eutectic solvent choline chloride-oxalic acid

Sayahi

Gholami

Meheiseni

et al. 2020

Zeitschrift Für Naturforschung B

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An effective method based on choline chloride (ChCl)-oxalic acid (Ox) deep eutectic solvent was proposed for the synthesis of 4-azaphenanthrene-3,10-dione, 1,8-dioxo-octahydroxanthene and tetrahydrobenzo[b]pyran derivatives. The eutectic mixture worked as both the solvent and acidic catalyst for conversion. The impacts of different variables, including the composition and volume of ChCl-Ox, and temperature, on reaction yield were studied for optimization. The crucial advantages of this process are simplicity of the experimental procedure, high yields, short reaction times, high recyclability, and the use of safe and inexpensive components.

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Section: Resultsmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

One-pot multi-component process for the synthesis of 4-azaphenanthrene-3,10-dione, 1,8-dioxo-octahydroxanthene and tetrahydrobenzo[b]pyran derivatives catalyzed by the deep eutectic solvent choline chloride-oxalic acid

Sayahi

Gholami

Meheiseni

et al. 2020

Zeitschrift Für Naturforschung B

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“…In the search of alternative catalytic systems, ILs and task specific ILs have been used to catalyse both ester formation, [41,42] and the desilylation reaction. [43] It has been also reported that Sc(OTf) 3 /Ac 2 O mixtures can be efficient systems for the consecutive desilylation and acetylation of sugars and this mixture was also very efficient in our case (entry 6 in Table S1).…”

Section: Substratementioning

confidence: 99%

Supported Ionic Liquid‐Like Phases (SILLPs) as Immobilised Catalysts for the Multistep and Multicatalytic Continuous Flow Synthesis of Chiral Cyanohydrins

et al. 2019

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Supported Ionic Liquid‐Like Phases have been found to be efficient organocatalysts for the synthesis of cyanohydrin esters under solvent‐free conditions by an “electrophile‐nucleophile dual activation” based on hydrogen bond formation. The combination of multiple and consecutive multicatalytic steps in a single and integrated cascade process of organocatalytic SILLPs with commercially available supported Candida antarctica lipase type B (CAL‐B) has allowed developing an efficient process for the multicatalytic synthesis of enantiopure cyanohydrins under flow conditions.

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“…Modified zirconia catalyzes the process too [49], while tributylphosphine has been shown as an efficient catalyst for acylation reactions [50]. Task-specific ionic liquids have also been found to have very good catalytic performance in the acetylation of alcohols and phenols [51].…”

Section: Introductionmentioning

confidence: 99%

Sustainable Carbon-Based Materials as Heterogeneous Catalysts in Solvent-Free Acetylation Reactions

López-Coca

Izquierdo

Silvero

et al. 2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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The catalytic activity of six different carbons was tested in the solvent-free acetylation reaction of alcohols, phenols, and monosaccharides with acetic anhydride. Three commercial carbons—a basic activated carbon M (Merck KGaA), a moderately basic carbon gel X (Xerolutions S.L.), and an activated carbon N (Norit Netherland B.V.)—were studied. From these commercial carbons, three acidic activated carbons—M-S, X-S, and N-S—were obtained by treatment with sulfuric acid. All six carbons were characterized by means of nitrogen adsorption capacity, porosimetry, elemental organic analysis, X-ray photoelectron spectroscopy (XPS), and point of zero charge (PZC) determination. The experiments carried out showed good catalytic activity, the magnitude of which depended on the type of carbon used. The best catalyst was X-S, which combined high acidity with the largest mesoporous volume. Second in line was the commercial carbon M, which was the most basic. The protocol reported herein encompasses several of the characteristics related to the sustainability of chemical processes, such as the innocuous nature and the affordable cost of the catalytic material, the absence of reaction solvent, and the ease of reaction work-up.

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Task-oriented use of ionic liquids: efficient acetylation of alcohols and phenols

Cited by 23 publications

References 19 publications

One-pot multi-component process for the synthesis of 4-azaphenanthrene-3,10-dione, 1,8-dioxo-octahydroxanthene and tetrahydrobenzo[b]pyran derivatives catalyzed by the deep eutectic solvent choline chloride-oxalic acid

One-pot multi-component process for the synthesis of 4-azaphenanthrene-3,10-dione, 1,8-dioxo-octahydroxanthene and tetrahydrobenzo[b]pyran derivatives catalyzed by the deep eutectic solvent choline chloride-oxalic acid

Supported Ionic Liquid‐Like Phases (SILLPs) as Immobilised Catalysts for the Multistep and Multicatalytic Continuous Flow Synthesis of Chiral Cyanohydrins

Sustainable Carbon-Based Materials as Heterogeneous Catalysts in Solvent-Free Acetylation Reactions

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