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Methylation of alcohols with diazomethane

Neeman, M. and Caserio, Marjorie C. and Roberts, John D. and Johnson, Williams S. (1959) Methylation of alcohols with diazomethane. Tetrahedron, 6 (1). pp. 36-47. ISSN 0040-4020. doi:10.1016/0040-4020(59)80034-X.

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Alcoholic hydroxyl groups were methylated by diazomethane in the presence of catalytic amounts of fluoboric acid (FBA). Primary aliphatic and unhindered secondary alcohols gave 84–98% yields of methyl ethers, while tertiary and moderately hindered secondary alcohols afforded lower yields. The order of reactivity in the methylation of the isomeric butyl alcohols, as determined in competition experiments, was n > s > t, and of the epimeric cholestanols, 3β (e) > 3 α(a). The highly hindered alcoholic hydroxyl groups of isoborneol was not methylated by the new reagent. The methylation of weakly acidic phenols was catalyzed by FBA. The new methylation reaction was used to prepare directly methyl ethers of desoxycorticosterone and of testosterone, and to convert ascorbic acid selectively to its 2:3:6-trimethyl ether.

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Additional Information:© 1959 Pergamon Press Ltd. Received 22 September 1958. We are indebted to the University of Wisconsin Research Committee for supporting a portion of this work from funds provided by the Wisconsin Alumni Research Foundation; to Professor Harlan L. Goering and Mr. Donald W. Larsen for preliminary analyses by vapor phase chromatography; and to Mr. Edgar Kiefer for his assistance in the early phase of this work.
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Wisconsin Alumni Research FoundationUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry2391
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Official Citation:M. Neeman, Marjorie C. Caserio, John D. Roberts, Williams S. Johnson, Methylation of alcohols with diazomethane, Tetrahedron, Volume 6, Issue 1, 1959, Pages 36-47, ISSN 0040-4020, (
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61530
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 21:50
Last Modified:10 Nov 2021 22:50

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