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. Palaciosa, Deyanira Angelesa, Leticia Lomasb and Rubén Gaviñoc
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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