Synthesis of aromatic ketones by acylation of aryl ethers with carboxylic anhydrides in the presence of zeolite H-β (H-BEA) in the absence of solvent1Dedicated to Professor Herman van Bekkum on the occasion of his 65th birthday.1

Smith, Keith; Zhao, Zhen‐Hua; Hodgson, P. K. G.

doi:10.1016/s1381-1169(98)00028-4

Cited by 78 publications

(24 citation statements)

References 28 publications

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“…Lewis acid plays a role of catalyst activity, with acetic anhydride catalyst produces acetyl-like ion in the first step on Friedel-Crafts acylation. According to Freese et al [21] and Smith et al [22], an acyl cation produced by reaction of the acetylating agent with the Zn 2+ -Za was proposed to be the critical species reacting with the adsorbed citronellal as a substrate, implying that reaction of the acyl cation-Zn 2+ -Za complex with the citronellal as a substrate was the rate-determining step [23].…”

Section: Activity and Selectivity Examinations Of Catalystsmentioning

confidence: 99%

Catalytic Activities of Fe3+- and Zn2+-Natural Zeolite on the Direct Cyclisation-Acetylation of (R)-(+)-Citronellal

Cahyono

Muchalal

Triyono

et al. 2014

Bull. Chem. React. Eng. Catal.

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An investigation on characterisation and catalytic ativities of modified natural zeolite on cyclisationacetylation reaction of (R)-(+)-citronellal was performed. The experimental works involved the isolation of (R)-(+)-citronellal from Javanese citronella (Cymbopogon winterianus) oil by vacuum fractional distillation, the determination of its enantiomers, and the preparation and characterisation of different catalysts i.e. H-natural zeolite (H-Za), Fe 3+ -natural zeolite (Fe 3+ -Za), and Zn 2+ -natural zeolite (Zn 2+ -Za), followed by the examination of their activity and selectivity on cyclisation-acetylation reaction of (R)-(+)-citronellal. The isolated citronellal contained 88.21 ee.% of (R)-(+)-citronellal. The crystallinity and the morphology of the modified zeolites showed that the natural zeolite from Malang Indonesia has the main component of mordenite-type zeolite. The main products of cyclisation-acetylation of (R)-(+)-citronellal were isopulegyl acetate (IPA) and neo-isopulegyl acetate (NIPA). Fe 3+ -Za catalyst showed the highest activity towards IPA and NIPA production but its stereoselectivity was slightly lower than that of Zn 2+ -Za catalyst. It is shown that Lewis acidity plays the role in the formation of acetyl ionic from acetic anhydride.

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Section: Activity and Selectivity Examinations Of Catalystsmentioning

confidence: 99%

Catalytic Activities of Fe3+- and Zn2+-Natural Zeolite on the Direct Cyclisation-Acetylation of (R)-(+)-Citronellal

Cahyono

Muchalal

Triyono

et al. 2014

Bull. Chem. React. Eng. Catal.

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“…This ester has to be either separated or further isomerised to ketone by Fries rearrangement. The ring acylation of phenol has been reported in the literature using ZSM-5 [9][10][11][12][13] or BEA [14,15] zeolite as catalyst, but the reaction of diphenols has been scarcely investigated. With bulky reactants, large pore solids are preferred and we report here the acylation of resorcinol on reducible transition metal cations deposited on a mesoporous support K10.…”

Section: Acylation By Heterogeneous Catalysismentioning

confidence: 99%

An Environmentally Friendly Route for the Synthesis of Benzofurane Derivatives using Selective Ring Acylation of Resorcinol

Békássy¹,

Ágai²,

Farkas³

et al. 2007

Catal Lett

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International audienceThe synthesis of 2,2-dimethyl-2,3-dihydrobenzofuran- 6-ol, an important intermediate for benzofurane derivatives having pharmaceutical activity, is achieved by an environmentally friendly pathway. Whereas the current synthesis method, based on resorcinol dimethylether, uses or produces harmful, corrosive and dangerous reagents/materials, the procedure proposed here achieves 60% preparative yield for the selective direct ring acylation of resorcinol with isobutyryl chloride, using a solvent-free reaction catalysed by solid acids

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“…Furthermore, using acetic anhydride over Hβ (0.15 g per 5 mmol of anisole) in the absence of solvent at 120 °C for 2 h gave exclusively paramethoxyacetophenone (Scheme 9; R = R′ = Me) in 98% yield [115].…”

Section: Regioselective Acylation Of Aromatic Compoundsmentioning

confidence: 99%

Regioselective Electrophilic Aromatic Substitution Reactions over Reusable Zeolites

Smith¹,

El‐Hiti²

2006

COC

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Synthesis of aromatic ketones by acylation of aryl ethers with carboxylic anhydrides in the presence of zeolite H-β (H-BEA) in the absence of solvent1Dedicated to Professor Herman van Bekkum on the occasion of his 65th birthday.1

Cited by 78 publications

References 28 publications

Catalytic Activities of Fe3+- and Zn2+-Natural Zeolite on the Direct Cyclisation-Acetylation of (R)-(+)-Citronellal

Catalytic Activities of Fe3+- and Zn2+-Natural Zeolite on the Direct Cyclisation-Acetylation of (R)-(+)-Citronellal

An Environmentally Friendly Route for the Synthesis of Benzofurane Derivatives using Selective Ring Acylation of Resorcinol

Regioselective Electrophilic Aromatic Substitution Reactions over Reusable Zeolites

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