The condensation of hydroquinone monobenzyl ether in the presence of several bases gives a mixture of cyclic oligomers. Using p-benzyloxyphenol, paraformaldehyde, and NaOH in 45:82:1 molar ratio in refluxing xylene, p-(benzyloxy)calix[8]arene (2) was selectively produced in 48% isolated yield. Compound 2 was also functionalized at the lower rim with acetoxy, methyl, pentyl, [(ethyloxy)carbonyl]methyl, and [(N,N-diethylamino)carbonyl]methyl groups. Replacement of the benzyl groups on these compounds allowed for the first time the high-yield syntheses of calix[8]hydroquinone and its derivatives.
p-(Benzyloxy)Calix[8]Arene: One Pot Synthesis and Functionalization / Casnati, Alessandro; R., Ferdani; Pochini, Andrea; Ungaro, Rocco. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 62:(1997), pp. 6236-6239. [10.1021/jo970620r]
p-(Benzyloxy)Calix[8]Arene: One Pot Synthesis and Functionalization
CASNATI, Alessandro;POCHINI, Andrea;UNGARO, Rocco
1997-01-01
Abstract
The condensation of hydroquinone monobenzyl ether in the presence of several bases gives a mixture of cyclic oligomers. Using p-benzyloxyphenol, paraformaldehyde, and NaOH in 45:82:1 molar ratio in refluxing xylene, p-(benzyloxy)calix[8]arene (2) was selectively produced in 48% isolated yield. Compound 2 was also functionalized at the lower rim with acetoxy, methyl, pentyl, [(ethyloxy)carbonyl]methyl, and [(N,N-diethylamino)carbonyl]methyl groups. Replacement of the benzyl groups on these compounds allowed for the first time the high-yield syntheses of calix[8]hydroquinone and its derivatives.| File | Dimensione | Formato | |
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