2000
DOI: 10.3184/030823400103166715
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Friedel-Crafts Benzylation of 1,4-dialkoxybenzenes – Cleavage and Rearrangement of Esters and Methoxymethyl Ethers in ZnCl2 Montmorillonite K10 Clay

Abstract: Benzylation of p-dialkoxybenzenes can be achieved through the use of modified montmorillonite K10 clay. For the first time, syntheses of nitro-diarylmethanes were obtained by Friedel-Crafts alkylation with good yields. In the case of p-methoxymethyl phenyl ether and phenyl ester, selectivity favoring Fries rearrangement over benzylation is reported.

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Cited by 8 publications
(5 citation statements)
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“…Also, the first- and second-generation dendrimers were prepared as materials; the details are shown in the Supporting Information. Subsequently, the phenolic hydroxy group of hydroquinone ( 2 ) was protected with the MOM group to afford compound 3 in 75% yield, which was then treated with I 2 and Hg(OAc) 2 to provide compound 4 in 80% yield. Deprotection of 4 with HCl furnished the key intermediate diphenol 5 in 95% yield.…”
mentioning
confidence: 99%
“…Also, the first- and second-generation dendrimers were prepared as materials; the details are shown in the Supporting Information. Subsequently, the phenolic hydroxy group of hydroquinone ( 2 ) was protected with the MOM group to afford compound 3 in 75% yield, which was then treated with I 2 and Hg(OAc) 2 to provide compound 4 in 80% yield. Deprotection of 4 with HCl furnished the key intermediate diphenol 5 in 95% yield.…”
mentioning
confidence: 99%
“…The resulting solid was dried at 80 °C for 12 h, to provide 1.9036 g of a white powder. From this, 0.5036 g were used as such and constituted the homogenous catalyst (M1) and the remaining 1.5 g were supported on montmorillonite K10 to obtain 1.22 mmol Zn per g of support in dry methanol to provide the heterogeneous catalyst (MM1) [13]. Upon concentration in vacuo, MM1 was finally activated at 120 °C overnight.…”
Section: Conception Of Biocatalystsmentioning
confidence: 99%
“…After cooling, the mixture was filtered on celite and the filtrate was evaporated to dryness. The residue was dried at 80°C for 12 h and then mixed with montmorillonite K10 in dry methanol to obtain 1.22 mmol Zn per g of support (15). Activation of this catalyst was performed at 120°C overnight (15).…”
Section: Preparation Of the Biosourced Catalyst (Biocat)mentioning
confidence: 99%