Iron(III) Chloride as a Lewis Acid in the Friedel-Crafts Acylation Reaction

Miles, William H.; Nutaitis, Charles F.; Anderton, Christian A.

doi:10.1021/ed073p272

Cited by 15 publications

(8 citation statements)

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“…It is known that CeO 2 is amphoteric which influences its acidic and basic properties. Acidity of 10 wt% FeO-CaO-EIM is related to presence of iron + 3 possessing Lewis acidity [32] in the form of Ca 2 Fe 2 O 5 .…”

Section: Catalyst Characterization Resultsmentioning

confidence: 99%

Aldol Condensation of Cyclopentanone with Valeraldehyde Over Metal Oxides

et al. 2019

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Kinetics of the cross aldol condensation of valeraldehyde with cyclopentanone was investigated in a batch reactor under atmospheric pressure at 130 °C using heterogeneous metal modified oxides, such as CeO 2 -MgO, FeO-MgO, FeO-CaO as well as pristine CaO as catalysts. The catalysts were prepared either by evaporation impregnation or deposition precipitation methods and characterized by XRD, TEM, SEM, nitrogen adsorption, ammonia and CO 2 TPD. The results revealed that an optimum amount of strong basic sites gives the highest ratio between cross condensation and self-condensation products of valeraldehyde. The highest yield of the desired product 2-pentylidenecyclopentanone (66%) was obtained with FeO-MgO prepared by the deposition precipitation methods. Graphical AbstractCross-condensation of valeraldehyde with cyclopentanone was investigated over heterogeneous Fe-CaO, CeO-MgO, FeO-CaO and CaO catalysts at 130 °C using cyclopentanone as a solvent and reactant. The highest yield of the desired product, 2-pentylidene-cyclopentanone, finding applications as fragrances, flavours and pharmaceuticals, was 66% obtained over FeO-MgO catalyst exhibiting both acid and basic sites.

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Section: Catalyst Characterization Resultsmentioning

confidence: 99%

Aldol Condensation of Cyclopentanone with Valeraldehyde Over Metal Oxides

et al. 2019

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“…The most widely employed Lewis acid for that reaction is aluminum chloride, although several other reagents also present appreciable reactivity . The safety and handling problems of aluminum chloride are not easily addressed and also the use of metal halides can causes problems associated with the formation of strong complexes between the product (ketone) and the metal halide catalyst . Therefore, new catalytic approaches are still receiving attention for the development of Friedel‐Craft reactions.…”

Section: Introductionmentioning

confidence: 99%

Efficient Solvent‐Free Friedel‐Crafts Benzoylation and Acylation of m‐Xylene Catalyzed by N‐Acetylpyrazine‐2‐carbohydrazide‐Fe(III)‐chloro Complexes

et al. 2018

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Reaction of N‐acetylpyrazine‐2‐carbohydrazide (H2L) with anhydrous Fe(II) or Fe(III) chloride in CH3CN or in MeOH leads to the mononuclear [Fe(κNN'O‐HL)Cl2] (1) or binuclear [Fe(κNN'O‐HL)Cl(μ‐OMe)]2 (2) Fe(III) complex, respectively. These complexes are characterized by elemental analysis, ESI‐MS, IR spectroscopy, single‐crystal X‐ray crystallography, electrochemical techniques and DFT calculations. The theoretical calculations indicate that the three single‐electron sequential reductions of 1 are centred at the metal, at the pyrazine group and at both, respectively. The catalytic activity of 1 and 2 was screened towards Friedel‐Crafts benzoylation and acylation of m‐xylene. The effects of reaction parameters, such as catalyst amount, reaction time and temperature, were studied and, under optimal conditions, 96% yield of 2,4‐dimethylbenzophenone and 20% yield of 2,4‐dimethylacetophenone were obtained, respectively. Complex 1 exhibited the highest activity in both reactions. The structural and electrochemical properties were supported by theoretical calculations and the importance of the Lewis acid character of the catalyst in the promotion of this catalytic reaction is discussed.

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“…The microscale reaction allows for the inclusion of more exotic aldehydes and ketones without unreasonable expense, however, even for classes with relatively large numbers of students. The preparation of the required benzaldehyde (via oxidation of the corresponding benzylic alcohol [22]) or acetophenone (via Friedel-Crafts acylation [2,23,24]) can be used to extend the project aspect of the experiment into a multistep synthesis experience. Finally, spectroscopic data for substituted chalcones is abundant in the literature, including UV-vis (25), IR (26 ), and 1 H and 13 C NMR (27)(28)(29)(30)(31)(32).…”

Section: Scheme IImentioning

confidence: 99%

Preparing Students for Research: Synthesis of Substituted Chalcones as a Comprehensive Guided-Inquiry Experience

et al. 2002

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A guided inquiry experiment involving the synthesis and characterization of substituted benzalacetophenones (chalcones) is described. The chalcones are produced in the aldol condensation of substituted benzaldehydes with substituted acetophenones. Each student is assigned a different target chalcone and conducts online and printed literature searches on the target. After completing the synthesis and purification of their product, the students compare their data with those found in the literature.

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Iron(III) Chloride as a Lewis Acid in the Friedel-Crafts Acylation Reaction

Cited by 15 publications

References 0 publications

Aldol Condensation of Cyclopentanone with Valeraldehyde Over Metal Oxides

Aldol Condensation of Cyclopentanone with Valeraldehyde Over Metal Oxides

Efficient Solvent‐Free Friedel‐Crafts Benzoylation and Acylation of m‐Xylene Catalyzed by N‐Acetylpyrazine‐2‐carbohydrazide‐Fe(III)‐chloro Complexes

Preparing Students for Research: Synthesis of Substituted Chalcones as a Comprehensive Guided-Inquiry Experience

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