Short Report

 

A Mild and Efficient Method for the Chemoselective Synthesis of Acylals from Aromatic Aldehydes and their Deprotections Catalyzed by Sulfated Zirconia

 

Guillermo E. Negrón^*,a, Laura N. Palacios^a, Deyanira Angeles^a, Leticia Lomas^b and Rubén Gaviño^c

 

^a Departamento de Ciencias Básicas, UAM, Av. San Pablo No. 180, 02200 México D. F., México. * e-mail: gns@correo.azc.uam.mx

^b Departamento de Química, UAM, Av. San Pablo No. 180, 02200 México D. F., México

^c Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, 04510 México D. F., México

 

Received: November 17, 2004
Published on the web: April 26, 2005

 

Abstract

Aldehydes can be converted to acylals by treatment with acetic anhydride in the presence of sulfated zirconia in excellent yield at 0^°C. Ketones and aliphatic aldehydes are found to be unaffected under the reaction conditions. The deprotection of the resulting acylals is achieved using the same catalyst at 60 ^oC. The catalyst can be reused in two cycles without losing its activity.

Keywords: acylals, sulfated zirconia, protection, deprotection

 

Resumo

Aldeídos podem ser convertidos a acilas por tratamento com anidrido acético na presença de zircônia sulfatada a 0 ^oC, com excelentes rendimentos. Cetonas e aldeídos alifáticos não são afetados nessas condições de reação. À desproteção das acilas resultantes é obtida usando-se o mesmo catalisador a 60 ^oC. O catalisador pode ser reutilizado por duas vezes sem perder sua atividade.

 

Acknowledgements

The authors are indebted to Consejo Nacional de Ciencia y Tecnología (CONACyT) for partial financial support (Project No. 33366-E).

 

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