tert-Butylation of phenols using tert-butyl alcohol in the presence of FeCl3-modified montmorillonite K10

Shinde, Ajit B.; Shrigadi, Nilesh B.; Samant, Shriniwas D.

doi:10.1016/s0926-860x(03)00612-4

Cited by 42 publications

(25 citation statements)

References 9 publications

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“…Tetrazoles as a group of heterocyclic compounds are reported to possess a broad spectrum of biological activities such as antibacterial, 1 antifungal, 2 antiviral, 3-5 analgesic, 6,7 anti-inflammatory, [8][9][10] [41][42][43][44][45][46][47][48] were commonly used to improve the catalytic abilities of montmorillonites. These methods require a large excess of sodium azide, longer reaction time, and expensive metals.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, several heterogeneous catalytic systems [32][33][34][35][36][37][38][39][40] using nanocrystalline ZnO, Zn/Al HT, 32 Zn hydroxyapatite, 33 38 ZnS, 39 and natural natrolite zeolite 40 were reported. Metal-modified montmorillonites and zeolite were reported widely, and many metals, such as Cu, Zn, Mn, Fe, Cu, V, Mo, Al and Co [41][42][43][44][45][46][47][48] were commonly used to improve the catalytic abilities of montmorillonites. These methods require a large excess of sodium azide, longer reaction time, and expensive metals.…”

Section: Introductionmentioning

confidence: 99%

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A novel approach for the synthesis of 5-substituted-1H-tetrazoles

Akhlaghinia¹,

Rezazadeh²

2012

J. Braz. Chem. Soc.

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Uma série de 1H-tetrazóis-5-substituídos (RCN 4 H) foi sintetizada pela reação de cicloadição de diferentes aril e alquil nitrilas com azida de sódio em DMSO, usando CuSO 4 •5H 2 O como catalisador. Uma grande variedade de aril nitrilas sofreu cicloadição [3+2], obtendo-se os correspondentes tetrazóis sob condições reacionais brandas. O catalisador utilizado é obtido facilmente e ambientalmente correto. Tempos de reação curtos, bons a excelentes rendimentos, processo seguro e simples tornam este método uma contribuição atrativa e útil à presente síntese orgânica de 1H-tetrazóis-5-substituídos.A series of 5-substituted-1H-tetrazoles (RCN 4 H) have been synthesized by cycloaddition reaction of different aryl and alkyl nitriles with sodium azide in DMSO using CuSO 4 •5H 2 O as catalyst. A wide variety of aryl nitriles underwent [3+2] cycloaddition to afford tetrazoles under mild reaction conditions in good to excellent yields. The catalyst used is readily available and environmentally friendly. Short reaction times, good to excellent yields, safe process and simple workup make this method an attractive and useful contribution to present organic synthesis of 5-substituted-1H-tetrazoles.Keywords: 5-substituted-1H-tetrazole, arylnitriles, sodium azide, CuSO 4 •5H 2 O, cycloaddition reaction IntroductionThe chemistry of heterocyclic compounds has been an interesting field of study for a long time. Tetrazoles as a group of heterocyclic compounds are reported to possess a broad spectrum of biological activities such as antibacterial, 1 antifungal, 2 antiviral, 3-5 analgesic, 6,7 anti-inflammatory, [8][9][10] [41][42][43][44][45][46][47][48] were commonly used to improve the catalytic abilities of montmorillonites. These methods require a large excess of sodium azide, longer reaction time, and expensive metals. Moreover, the cycloaddition is too slow A Novel Approach for the Synthesis of 5-Substituted-1H-tetrazoles J. Braz. Chem. Soc. 2198 to be synthetically useful except when strong electronwithdrawing groups activate the nitrile compounds.Today's stringent environmental and legislative concerns demand for the green methods that reduce the use of toxic and corrosive reagents and stop the formation of inorganic wastes. 49 However, it has been also observed that the catalysts employed are not always eco-friendly and because of this, serious environmental pollution often results. Therefore, in the area of green synthesis, the development of environmentally friendly alternatives is desirable for the synthesis of tetrazoles. 50 Recently, we have studied the application of cupric sulfate pentahydrate in the trimethylsilylation of alcohols and phenols, 51 and perceived that cupric sulfate pentahydrate as a mild Lewis acid, which is readily available, might be a useful catalyst for the synthesis of 5-substituted-1H-tetrazoles. In this paper we report a new process for the synthesis of 5-substituted 1-H-tetrazoles using cupric sulfate pentahydrate as a safe, environmentally benign, and inexpensive catalyst. ExperimentalThe p...

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A novel approach for the synthesis of 5-substituted-1H-tetrazoles

Akhlaghinia¹,

Rezazadeh²

2012

J. Braz. Chem. Soc.

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“…Therefore, we attempted to reduce the amount of KSF in this nitration process. Herein we wish to report a new catalytic system of Yb-Mo-HKSF impregnated by other metal salts [28][29][30][31][32][33][34][35][36][37][38][39] for the nitration of phenolic Moreover, it should be emphasized here that this catalytic nitration is a heterogeneous catalytic process and these catalysts can be easily recovered from the reaction mixture by filtration. These catalysts can be reused many times without degradation after being reactivated by heating in an oven at 120 o C. In this catalytic system, we utilized CuCl 2 impregnated…”

Section: Introductionmentioning

confidence: 99%

Nitration of phenolic compounds by metal salts impregnated Yb-Mo-montmorillonite KSF

Yin¹,

Shi²

2008

Arkivoc

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“…Alkylation of p-cresol with t-butanol produces industrially important organic intermediates, such as 2-t-butyl-4-methylphenol (2-TBPC) and 2,6-di-tbutyl-4-methylphenol (2,6-DTBPC), which are widely used in antioxidants and polymerization inhibitors and in the manufacture of phenol resins [7]. Recently, many workers have been attention to the liquid phase or vapor phase t-butylation of phenols over solid acid catalysts, such as zeolites [9][10][11], clays [12], metal oxides [13], and mesoporous materials [14][15][16][17][18][19][20] including their modified catalysts; however, there have been a few to succeed in the di-t-butylation of phenols. We have considered one of the reasons is the deactivation of acidic sites by coke formation.…”

Section: Introductionmentioning

confidence: 99%

“…Tungstophosphoric acid (HPW) modified mesoporous zirconia and cobalt aluminophosphate were used for catalysts in the synthesis of t-butyl cresols in liquid or vapor phase [13,14]. However, they mainly discussed on the selective synthesis of mono butyl cresols.…”

Section: Introductionmentioning

confidence: 99%

The Di-t-butylation of p-cresol with t-butanol in Supercritical CO2 over Tungstophosphoric Acid Supported on Ordered Mesoporous Silica

2006

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Tungstophosphoric acid (HPW) supported on MCM-41 was an excellent catalyst for the t-butylation of p-cresol to 2,6-di-tbutyl-4-methylphenol (2,6-DTBPC) in supercritical CO 2 ; however, zeolites, H-Y and H-Beta, only gave 2-t-butyl-4-methylphenol (2-TBPC) because of their limitation in pore size. The yield of 2,6-DTBPC was maximized at 110°C, and further increase in temperature rather decreased the yield. The yield of 2,6-DTBPC was maximized at 10-11 MPa CO 2 pressure, and further increase of the pressure decreased in the conversion of phenol and the yield of 2,4-DTBC. The thermogravimetric analysis of used catalysts showed that the coke-formation was minimized in supercritical CO 2 compared to the other reaction media such as in liquid phase and in N 2 atmosphere.

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tert-Butylation of phenols using tert-butyl alcohol in the presence of FeCl3-modified montmorillonite K10

Cited by 42 publications

References 9 publications

A novel approach for the synthesis of 5-substituted-1H-tetrazoles

A novel approach for the synthesis of 5-substituted-1H-tetrazoles

Nitration of phenolic compounds by metal salts impregnated Yb-Mo-montmorillonite KSF

The Di-t-butylation of p-cresol with t-butanol in Supercritical CO2 over Tungstophosphoric Acid Supported on Ordered Mesoporous Silica

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