7549-37-3Relevant articles and documents
Method for the selective formation of dimethyl acetals in the presence of hydroxylamine
Mickelsen, Ky J.,Tajc, Chelsea M.,Greenwood, Kevin R.,Browder, Cindy C.
experimental part, p. 186 - 194 (2011/10/31)
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 corresponding dimethyl acetal as the sole product in good to excellent yield. Unsaturated and hindered aldehydes required stoichiometric amounts of hydroxylamine but provided dimethyl acetals as the major product in typically excellent yield. In some cases, the corresponding oxime was also observed but may be separated from the acetal by flash column chromatography or distillation. The involvement of an intermediate oxime compound is postulated. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Taylor & Francis Group, LLC.
A facile procedure for acetalization of aldehydes and ketones catalyzed by cerium(III) trifluoromethanesulfonate
Ono, Fumiaki,Inatomi, Yoshiko,Tada, Yuusuke,Mori, Masaki,Sato, Tsuneo
experimental part, p. 96 - 97 (2009/11/30)
Aldehydes and ketones are readily protected in the presence of trialkyl orthoformate and a catalytic amount of cerium(III) trifluoromethanesulfonate under mild conditions to give the corresponding acetals in good to excellent yields. Due to the mild reaction conditions, this method is compatible with acid-sensitive substrates. Copyright