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41.1.1.1.29 Method 29: Substitution of Sulfates

DOI: 10.1055/sos-SD-041-00002

Aitken, R. A.; Aitken, K. M.Science of Synthesis, (20104146.

Reactions of mono- or dialkyl sulfates with alkali metal nitrites were of interest in the early 20th century as a less expensive alternative to reacting alkyl halides with silver(I) nitrite. Monoalkyl sulfates are found to react with metal nitrites under solvent-free conditions (with a few drops of water added) with relatively low yields; the best results are shown in Scheme 53.[‌207‌] Patents have also been published describing the conversion of sodium methyl sulfate into nitromethane[‌208‌] and sodium ethyl sulfate into nitroethane.[‌209‌]

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