Benzoyl chloride → N-Hydroxy-N-methylbenzamide

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Reaction Steps

The n-methyl hydroxylamine-HCl and m-pyrol were combined in a 250 milliliter (ml) round bottomed flask, cooled in an ice bath, and allowed to mix until most of the salt dissolved. The benzoyl chloride was slowly added over 15 minutes and allowed to stir for 1 hour. The water was then added and the product extracted three times with ethyl acetate. The ethyl acetate was evaporated from the product, and the product dissolved in 200 ml of 5% NaOH. The product was then extracted three times with 100 ml methylene chloride. The aqueous layer was acidified with H2S04 to a pH of 6 and then extracted three times with 100 ml of ethyl acetate. The organic layer was dried with MgS04 and silica gel, and evaporated to dryness yielding n-methylbenzohydroxamic acid.

Provenance & Evidence