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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 8
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Original Articles

Efficient Tetrahydropyranylation of Phenols and Alcohols Catalyzed by Supported Mo and W Keggin Heteropolyacids

G. P. Romanelli LADECOR, Laboratorio de Estudio de Compuestos Orgánicos, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, La Plata, Argentina; CINDECA, Centro de Investigación en Procesos Catalíticos, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata – CONICET, La Plata, Argentina
,
P. G. Vázquez CINDECA, Centro de Investigación en Procesos Catalíticos, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata – CONICET, La Plata, Argentina
,
L. R. Pizzio CINDECA, Centro de Investigación en Procesos Catalíticos, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata – CONICET, La Plata, Argentina
,
C. V. Cáceres CINDECA, Centro de Investigación en Procesos Catalíticos, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata – CONICET, La Plata, Argentina
,
M. N. Blanco CINDECA, Centro de Investigación en Procesos Catalíticos, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata – CONICET, La Plata, Argentina
&
J. C. Autino LADECOR, Laboratorio de Estudio de Compuestos Orgánicos, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, La Plata, ArgentinaCorrespondence[email protected]
Pages 1359-1365 | Received 15 Jun 2002, Published online: 15 Aug 2006
 
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Abstract

The protection of phenols as tetrahydropyranyl acetals is studied using supported Keggin heteropolyacids as catalysts, specifically molybdophosphoric or tungstophosphoric acids supported on silica. Phenol tetrahydropyranyl acetals are obtained in short times at room temperature with excellent yields. Protection of alcohols is also performed under mild conditions using both supported heteropolyacids, with yields ranging between good and quantitative. The reactions are clean and their workup is very simple. The use of these solid catalysts allows replacing the usual soluble inorganic acids, contributing to waste reduction.

Acknowledgments

Financial support of Universidad Nacional de La Plata, CONICET and Agencia Nacional de Promoción Científica y Tecnológica (Argentina) is gratefully acknowledged.

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