Synthesis of n-heptanal oxime

Preparation of n-heptanal oxime

Alternative Names: heptanal, oxime; enanthaldoxime

Preparation of n-heptanal oxime (heptanal, oxime; enanthaldoxime)

Preparation of n-heptanal oxime (heptanal, oxime; enanthaldoxime)

A 1-litre three-necked flask is fitted with an efficient mechanical stirrer, a reflux condenser and a thermometer. 141 ml (115 g) of 1-heptanal 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 n-heptonitrile and n-heptanal oxime) passes over first, and as soon as the temperature is constant the n-heptanal oxime distills at 103-107°/6 mm yielding about 110 g. of n-heptanal oxime, which slowly solidifies on cooling and melts at 44-46° C. A very pure product may be obtained recrystallization from 60% ethyl alcohol (25 g of n-heptanal oxime to 70 ml of solvent) and then melts at 53-55° C.

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

IUPAC Name

(NE)-N-heptylidenehydroxylamine

InChI

InChI=1S/C7H15NO/c1-2-3-4-5-6-7-8-9/h7,9H,2-6H2,1H3/b8-7+

InChI Key

BNYNJIKGRPHFAM-BQYQJAHWSA-N

Canonical SMILES

CCCCCCC=NO

Isomeric SMILES

CCCCCC/C=N/O

Depositor-Supplied Synonyms

Heptanal oxime, Heptanal, oxime, Enanthaldoxime, NSC 2191, EINECS 211-086-6, BRN 1721246, 629-31-2, heptanaloxime, N-heptaldoxime, AC1NS51V, AC1Q4U5S, CHEMBL137790, SCHEMBL1965261, SCHEMBL8463189, (NE)-N-heptylidenehydroxylamine, (E)-N-heptylidene-hydroxylamine, AR-1J1521, AKOS006272319, LS-74238, FT-0655146, X6225, 3-01-00-02850 (Beilstein Handbook Reference), S14-1045

Removed Synonyms

CID5354166, 63918-94-5

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