Efficient preparation of ketones from N-(ethoxymethylene) aniline and organometallic reagents

L Strekowski, RL Wydra, MT Cegla…

Index: Strekowski, Lucjan; Wydra, Roman L.; Cegla, Marek T.; Czarny, Agnieszka; Patterson, Steven Journal of Organic Chemistry, 1989 ,  vol. 54,  # 26  p. 6120 - 6123

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Citation Number: 20

Abstract

Phenylmagnesium bromide was reacted with compound 1 in ether to give N- (phenylmethy1ene) aniline (3a), which could be hydrolyzed to benzaldehyde? Quantitative yields of 3a were obtained for the reactions conducted with either 1 equiv or a large excess of the Grignard reagent. The latter result can be explained assuming that ti) the initial adduct 2a does not decompose to Schiff s base 3a before quenching the mixture or (ii) the adduct ...