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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: ptb969 on April 04, 2008, 08:32:16 AM

Title: Oxim synthesis
Post by: ptb969 on April 04, 2008, 08:32:16 AM

Hallo,
today I have read an article describing a way to synthesize oxim from methyl acetoacetate using NaNO₂ in acetic acid (See the scheme attached here). I do not really figure out the mechanism of this reaction.

Could any one give a suggestion.
As far as I know, to prepare an oxim, people start from a carbonyl compound reacting with hydroxyl amine.
Best regards,
CPC

Title: Re: Oxim synthesis
Post by: Dan on April 04, 2008, 08:55:44 AM

NaNO₂ in acid can generate NO⁺, so I expect that's your electrophile. The enol from MAA will be your nucleophile.

Title: Re: Oxim synthesis
Post by: ptb969 on April 04, 2008, 09:08:44 AM

Oh, Dan,
thank you very much for a quick suggestion. I appreciate that very much.
You know I have prepared oxim only once so I am not quite experienced with that.

Sincerely,
CPC