Bismuth(III) salts as convenient and efficient catalysts for the selective acetylation and benzoylation of alcohols and phenols

Mohammadpoor‐Baltork, Iraj; Aliyan, Hamid; Khosropour, Ahmad Reza

doi:10.1016/s0040-4020(01)00521-x

Cited by 103 publications

(25 citation statements)

References 26 publications

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“…In regards to the synthesis of p-and o-HBP (or other substituted benzophenones) or benzyl benzoates via c-or o-benzoylation, respectively, papers in the literature describe the use of benzoyl chloride or benzyl trichloride also with various homogeneous catalysts: AlCl3 for phenol (and phenol derivatives containing 2,2,6,6,-tetramethylpiperidine) [95], Cu(OTf)2 and Sn(OTf)2 for anisole and veratrole [96,97], Bi(III) salts for phenol [98] and Hf(OTf)4 for phenol [99], even with carboxylic acids [100].…”

Section: Introductionmentioning

confidence: 99%

Zeolite Catalysts for Phenol Benzoylation with Benzoic Acid: Exploring the Synthesis of Hydroxybenzophenones

et al. 2015

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Abstract:In this paper, we report on the reaction of phenol benzoylation with benzoic acid, which was carried out in the absence of solvent. The aim of this reaction is the synthesis of hydroxybenzophenones, which are important intermediates for the chemical industry. H-beta zeolites offered superior performance compared to H-Y, with a remarkably high conversion of phenol and high yields to the desired compounds, when using a stoichiometric amount of benzoic acid. It was found that the reaction mechanism did not include the intramolecular Fries rearrangement of the primary product phenyl benzoate, but indeed, the bimolecular reaction between phenyl benzoate and phenol mainly contributed to the formation of hydroxybenzophenones. The product distribution was greatly affected by the presence of Lewis-type acid sites in H-beta; it was suggested that the interaction between the aromatic ring and the electrophilic Al 3+ species led to the preferred formation of o-hydroxybenzophenone, because of the decreased charge density on the C atom at the para position of the phenolic ring. H-Y zeolites were efficient than H-beta in phenyl benzoate transformation into hydroxybenzophenones.

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Section: Introductionmentioning

confidence: 99%

Zeolite Catalysts for Phenol Benzoylation with Benzoic Acid: Exploring the Synthesis of Hydroxybenzophenones

et al. 2015

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“…Formylation using ethyl formate offers numerous advantages such as simple work-up and easy accessibility of the reagent at relatively low rate. Common metal triflates generally used for this reaction are In(OTf) 3 (7), Ce(OTf) 4 (8), and Bi(III)salts (9 (12), TiCl 3 (OTf) (13), cerium polyoxometalate (14), silicabonded N-propyl sulfamic acid (15), and sulfuric acid ([3-(3-silicapropyl)sulfanyl] propyl)ester (16) are the various solid acid catalysts used for formylation with ethyl formate.…”

Section: Introductionmentioning

confidence: 99%

Formylation and acetylation of alcohols using Amberlyst-15^®as a recyclable heterogeneous catalyst

Singh

Bhanage

Nagarkar

2012

Green Chemistry Letters and Reviews

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Formylation of alcohols with ethyl formate in the presence of solid acidic resin Amberlyst-15 as a catalyst was carried out. Good to excellent yields of products were obtained. The catalyst also works for the acetylation of alcohols with ethyl acetate at reflux temperature. Simple work-up, reusability, nontoxicity, and stability of the catalyst are the advantages of this work as compared to conventional protocols.

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“…However, they are not stable under strongly acidic conditions. On the other hand, acetates serve as effective hydroxyl blocking agent which are stable to acidic conditions [15]. Thus one-pot conversion of TMS ethers to the corresponding acetates could be considered as a useful transformation in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

CAN/[nbp]FeCl4 as a reusable catalytic system for direct conversion of trimethylsilyl ethers to their acetates under microwave irradiation

Khosroupour¹,

Khodaei²,

Ghaderi³

2008

JICS

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A rapid and easy procedure for direct conversion of TMS-ethers to their acetates catalyzed by cerium(IV) ammonium nitrate (CAN) immobilized on n-butylpyridinium tetrachloroferrate ([nbp]FeCl 4 ) as a room temperature ionic liquid under microwave irradiation was developed. This methodology is enough mild so that the acid sensitive groups such as methoxy, furyl or thiophenyl were remained intact. No side products were observed by this method.

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Bismuth(III) salts as convenient and efficient catalysts for the selective acetylation and benzoylation of alcohols and phenols

Cited by 103 publications

References 26 publications

Zeolite Catalysts for Phenol Benzoylation with Benzoic Acid: Exploring the Synthesis of Hydroxybenzophenones

Zeolite Catalysts for Phenol Benzoylation with Benzoic Acid: Exploring the Synthesis of Hydroxybenzophenones

Formylation and acetylation of alcohols using Amberlyst-15^®as a recyclable heterogeneous catalyst

CAN/[nbp]FeCl4 as a reusable catalytic system for direct conversion of trimethylsilyl ethers to their acetates under microwave irradiation

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Bismuth(III) salts as convenient and efficient catalysts for the selective acetylation and benzoylation of alcohols and phenols

Cited by 103 publications

References 26 publications

Zeolite Catalysts for Phenol Benzoylation with Benzoic Acid: Exploring the Synthesis of Hydroxybenzophenones

Zeolite Catalysts for Phenol Benzoylation with Benzoic Acid: Exploring the Synthesis of Hydroxybenzophenones

Formylation and acetylation of alcohols using Amberlyst-15®as a recyclable heterogeneous catalyst

CAN/[nbp]FeCl4 as a reusable catalytic system for direct conversion of trimethylsilyl ethers to their acetates under microwave irradiation

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Formylation and acetylation of alcohols using Amberlyst-15^®as a recyclable heterogeneous catalyst