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Making Oximes - via hydroxylamine
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psypsy100

Joined: 09 Jun 2005
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Making Oximes - via hydroxylamine

 Thu Jun 09, 2005 5:04 am		 Reply with quote
I've read various procedures which discuss making a primary amine via the corresponding oxime. All of these procedures call for the ketone to be reacted with hydroxylamine hydrochloride. Could hydroxylamine sulfate be used, and if so, what changes to the procedure might be needed? The procedure I'm thinking of simply involves stirring the hydroxylamine, ketone and sodium acetate in MeOH/water.

Thanks
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anime

Joined: 13 Apr 2005
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Re: Making Oximes - via hydroxylamine

 Thu Jun 16, 2005 8:13 am		 Reply with quote
psypsy100 wrote:
I've read various procedures which discuss making a primary amine via the corresponding oxime. All of these procedures call for the ketone to be reacted with hydroxylamine hydrochloride. Could hydroxylamine sulfate be used, and if so, what changes to the procedure might be needed? The procedure I'm thinking of simply involves stirring the hydroxylamine, ketone and sodium acetate in MeOH/water.

Thanks



Yes it can, however you will need to adjust the amount of material to the correct molar equiv. Sodium bicarbonate or sodium carbonate can be used instead of the sodium acetate.
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the alchemist

Joined: 23 Jun 2005
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re: Making Oximes - via hydroxylamine

 Wed Jun 29, 2005 12:55 am		 Reply with quote
Add about 1.2 eq of a base like potassium carbonate and stir with your ketone and hydroxylamine salt overnight and you will have nice yields of oxime.

respect
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