ChemInform Abstract: EFFECT OF THE STRUCTURE OF ORGANOALUMINUM COMPOUNDS ON THE ALKYLATION OF PHENOL BY OLEFINS

Zorina, Anna V.; Michurov, Yu. I.; Gershanov, F. B.; Rutman, G. I.; Кучин, А. В.; Yur'ev, V. P.

doi:10.1002/chin.198032156

Chemischer Informationsdienst

1980

DOI: 10.1002/chin.198032156

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ChemInform Abstract: EFFECT OF THE STRUCTURE OF ORGANOALUMINUM COMPOUNDS ON THE ALKYLATION OF PHENOL BY OLEFINS

Anna V. Zorina¹,

Yu. I. Michurov²,

F. B. Gershanov³

et al.

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Cited by 2 publications

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“…The reaction of camphene with dihydroxybenzenes (resorcinol and pyrocatechol) in methylenechloride over wide-pore β-zeolite has been investigated. The products from O-alkylation (20-30% yield) and C-alkylation (20-35% yield) of the phenols were formed [4].Herein we report results of the alkylation of pyrocatechol (1) and resorcinol (9) by camphene (2) in the presence of aluminum phenoxide Al(OPh) 3 and aluminum isopropoxide Al(i-OPr) 3 .Aluminum phenoxide was chosen because it is one of the most active organoaluminum catalysts [5]. However, exchange can occur if Al(OPh) 3 is used to alkylate difunctional phenols.…”

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Alkylation of pyrocatechol and resorcinol by camphene

et al. 2007

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Alkylation of pyrocatechol and resorcinol by camphene in the presence of the organoaluminum catalysts aluminum phenoxide and aluminum isopropoxide was studied.Sterically hindered dihydroxyphenols containing bulky alkyl substituents in the position ortho to the hydroxyls are of great interest as intermediates for synthesizing antioxidants, metal-corrosion inhibitors, medicinal preparations, and agricultural chemicals [1,2].Alkylation of hydroquinone by camphene in the presence of aluminum phenoxide has been studied [3]. It was found that the reaction pathway of C-or O-alkylation depended significantly on the ratio of the starting compounds.The alkylation of polyfunctional phenols and their ethers in the presence of metal phenoxides, including aluminum phenoxide, has been little studied. The reaction of camphene with dihydroxybenzenes (resorcinol and pyrocatechol) in methylenechloride over wide-pore β-zeolite has been investigated. The products from O-alkylation (20-30% yield) and C-alkylation (20-35% yield) of the phenols were formed [4].Herein we report results of the alkylation of pyrocatechol (1) and resorcinol (9) by camphene (2) in the presence of aluminum phenoxide Al(OPh) 3 and aluminum isopropoxide Al(i-OPr) 3 .Aluminum phenoxide was chosen because it is one of the most active organoaluminum catalysts [5]. However, exchange can occur if Al(OPh) 3 is used to alkylate difunctional phenols. This is due to reaction of the catalyst and the reagent [6] as Al(OPh) 3 + HOC 6 H 4 OH → (PhO) 2 AlOC 6 H 4 OH + PhOH.The phenol produced by this reaction can undergo alkylation, thereby increasing the amount of side products. In order to avoid side reactions, Al(i-OPr) 3 was investigated as the catalyst.The yields of products from alkylation of pyrocatechol (1) by camphene (2) (Scheme 1, Table 1) depended substantially on the catalyst. The yield of products was 29% if Al(OPh) 3 was used; 54%, Al(i-OPr) 3 . The ratio of the starting compounds affected the selectivity of the reaction. The reaction of pyrocatechol and camphene formed the O-and C-alkylated products, the structures of which were established by IR, PMR, and 13 C NMR spectroscopy.Alkylation at 160°C formed a monoether of pyrocatechol with the isobornyl structure for the terpene substituent (3) as the main product regardless of the catalyst used. Terpenophenols 6, 7, and 8 were formed through C-alkylation with a 2:1 ratio of 1:2 in the presence of Al(i-OPr) 3 . In addition to these products, alkylation of pyrocatechol formed a mixture of isocamphyl (4) and isophenchyl (5) monoethers.Performing the reaction at 180-200°C alkylated the aromatic ring to form monosubstituted (84%) and dialkylated (13%) pyrocatechols.

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“…Aluminum phenoxide was chosen because it is one of the most active organoaluminum catalysts [5]. However, exchange can occur if Al(OPh) 3 is used to alkylate difunctional phenols.…”

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Alkylation of pyrocatechol and resorcinol by camphene

et al. 2007

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“…Initially, addition of phenol to aluminum phenoxide gives HAl(OC 6 H 5 ) 4 [20,21]. Initially, addition of phenol to aluminum phenoxide gives HAl(OC 6 H 5 ) 4 [20,21].…”

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10.1007/s11178-008-1007-x

2010

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The alkylation of phenol with camphene in the presence of boron trifluoride in glacial acetic acid was accompanied by tandem molecular rearrangement with formation of a mixture of ortho-and para-substituted phenols having 1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl and 5,5,6-trimethylbicyclo[2.2.1]hept-exo-2yl substituents. The same products were obtained by rearrangement of 1,7,7-trimethylbicyclo[2.2.1]hept-exo-2yloxybenzene under analogous conditions. Similar reactions performed in the presence of aluminum phenoxide as catalyst resulted in predominant formation of the corresponding ortho-substituted phenols.

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ChemInform Abstract: EFFECT OF THE STRUCTURE OF ORGANOALUMINUM COMPOUNDS ON THE ALKYLATION OF PHENOL BY OLEFINS

Cited by 2 publications

References 0 publications

Alkylation of pyrocatechol and resorcinol by camphene

Alkylation of pyrocatechol and resorcinol by camphene

10.1007/s11178-008-1007-x

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