Synthesis of octanaloxime

Preparation of octanaloxime (octan-1-one oxime; n-hydroxyoctan-1-imine; n-octylidenehydroxylamine; octanal, oxime, (1E)-)

Preparation of octanaloxime (octan-1-one oxime; n-hydroxyoctan-1-imine; n-octylidenehydroxylamine; octanal, oxime, (1E)-)

Preparation of octanaloxime (octan-1-one oxime; n-hydroxyoctan-1-imine; n-octylidenehydroxylamine; octanal, oxime, (1E)-)

A 1-litre three-necked flask is fitted with an efficient mechanical stirrer, a reflux condenser and a thermometer. 128.2 g of 2-octanone and a solution of 87 g of hydroxylamine hydrochloride in 150 ml of water are placed in the flask with vigorously stirring. Through a dropping funnel fitted into the top of the reflux condenser, a solution of 67 g of anhydrous sodium carbonate dissolved in 250 ml of water is added at such a rate that the temperature of the reaction mixture does not rise above 45° C. When all of the sodium carbonate solution is added the stirring is continued for 1 hour at room temperature. Then the upper layer is separated, washed with water, dried with anhydrous sodium or magnesium sulfate and purified by fraction distillation. A small fraction of the low boiling point (containing 2-octanone) passes over first, and as soon as the temperature is constant the octanaloxime distills at 106-108°/12 mm yielding about 90% of octanaloxime.

A text book of practical organic chemistry, by A. I. Vogel, 348, 1974

IUPAC Name

N-octylidenehydroxylamine

InChI

InChI=1S/C8H17NO/c1-2-3-4-5-6-7-8-9-10/h8,10H,2-7H2,1H3

InChI Key

GGZXEEFQIXMFBF-UHFFFAOYSA-N

Canonical SMILES

CCCCCCCC=NO

Depositor-Supplied Synonyms

Octanaloxime, 929-55-5, octan-1-one oxime, N-hydroxyoctan-1-imine, N-octylidenehydroxylamine, Octanal, oxime, (1E)-, SCHEMBL265367, SCHEMBL578937, AC1L394Y, CTK1D9207, CTK5H1913, GGZXEEFQIXMFBF-UHFFFAOYSA-N, 5966-43-8

Removed Synonyms

Caprylic aldehyde oxime, CID136720

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