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Methylation of Alcohols with Diazomethane

Caserio, Marjorie C. and Roberts, John D. and Neeman, M. and Johnson, William S. (1958) Methylation of Alcohols with Diazomethane. Journal of the American Chemical Society, 80 (10). pp. 2584-2585. ISSN 0002-7863. doi:10.1021/ja01543a056.

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Methylation of alcohols by the Williamson synthesis requires strongly basic conditions and there is no satisfactory general methylation procedure effective under neutral or mildly acidic conditions. In principle, diazomethane with an acidic catalyst should methylate alcohols, but the usual protonic acid, such as hydrochloric acid, is unsatisfactory because it is itself methylated with diazomethane. Fluoroboric acid, however, promised to serve as a useful catalyst since it would be consumed in reaction with diazoinethane only by some process involving rupture of a B-F bond. This expectation was indeed realized and a novel method has been developed for methylation of alcohols in high yields under mild conditions.

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Additional Information:© 1958 American Chemical Society. Received April 14, 1958.
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Caltech Gates and Crellin Laboratories of Chemistry2332
Issue or Number:10
Record Number:CaltechAUTHORS:20151020-153344670
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Official Citation:METHYLATION OF ALCOHOLS WITH DIAZOMETHANE Marjorie C. Caserio, John D. Roberts, M. Neeman, and William S. Johnson Journal of the American Chemical Society 1958 80 (10), 2584-2585 DOI: 10.1021/ja01543a056
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61346
Deposited By: Ruth Sustaita
Deposited On:21 Oct 2015 19:32
Last Modified:10 Nov 2021 22:47

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