Method for the selective formation of dimethyl acetals in the presence of hydroxylamine

KJ Mickelsen, CM Tajc, KR Greenwood…

Index: Mickelsen, Ky J.; Tajc, Chelsea M.; Greenwood, Kevin R.; Browder, Cindy C. Synthetic Communications, 2012 , vol. 42, # 2 p. 186 - 194

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Abstract

An inexpensive and mild method for the formation of dimethyl acetals from the corresponding aldehydes is achieved using hydroxylamine and methanol under neutral conditions at room temperature. Notably, the reaction is selective for aldehydes in the presence of ketones, rendering this an example of a chemoselective acetalization. For saturated, sterically accessible aldehydes, catalytic amounts of hydroxylamine may be employed to attain the ...