Synthesis of acetone oxime (acetoxime; propan-2-one oxime)

Preparation of acetone oxime

Preparation of acetone oxime (acetoxime; propan-2-one oxime)

Preparation of acetone oxime (acetoxime; propan-2-one oxime)

12.5 g of hydroxylamine hydrochloride is dissolved in 20 ml of water and the solution is placed in a 100 ml conical flask. 7 g of powdered sodium hydroxide dissolved in 20 ml of water, is added to previously prepared hydroxylamine hydrochloride solution. During the addition of sodium hydroxide the solution of hydroxylamine hydrochloride is cooled in ice-water. It is important that the sodium hydroxide must be accurately weighed out, for an excess will dissolve the acetone oxime. A thermometer is placed in the mixed solution, and when the temperature drops to 5-10° C 9.5 g (or 12 ml) of dry acetone are added with stirring in small quantities so that, the temperature does not rise above 15° C. The acetone oxime usually starts to crystallize when about half the acetone has been added. When the addition is complete, the mixture is allowed to stand in ice-water for additional 15 minutes. The solution is filtered and the crude acetone oxime is collected, yielding 12-13 g of crystalline product.  The acetone oxime so obtained contains the small amount of sodium chloride, but is otherwise almost pure for the most synthesis purposes. Crude acetone oxime is purified by crystallization from petroleum ether (with boiling point 60-80° C) or cyclohexane. The acetone oxime is freely soluble in water and in most organic liquids.

Practical organic chemistry, by F. G. Mann, 8, 1960

IUPAC Name

N-propan-2-ylidenehydroxylamine

InChI

InChI=1S/C3H7NO/c1-3(2)4-5/h5H,1-2H3

InChI Key

PXAJQJMDEXJWFB-UHFFFAOYSA-N

Canonical SMILES

CC(=NO)C

MeSH Synonyms

acetone, oxime, acetoxime, acetoxime, 2-(14)C-labeled, actone oxime

Depositor-Supplied Synonyms

Acetone oxime, Acetoxime, 127-06-0, propan-2-one oxime, 2-Propanone, oxime, Acetonoxime, Acetone, oxime, 2-Propanone oxime, beta-Isonitrosopropane, .beta.-Isonitrosopropane, CCRIS 5, UNII-QX74TFD64T, N-propan-2-ylidenehydroxylamine, PXAJQJMDEXJWFB-UHFFFAOYSA-N, NSC 7601, EINECS 204-820-1, BRN 1560146, AI3-52259, Acetoneoxime, propanone oxime, Propane-2-one oxime, ACETONE-OXIME, AC1Q2A1Q, AC1Q4SV0, N-isopropylidenehydroxylamine, ACMC-1C1J8, QX74TFD64T, A10507_ALDRICH, N-isopropylidene-hydroxylamine, Acetoxime; 2-Propanone oxime, KSC177C7T, (CH3)2C=NOH, AC1L270Q, WLN: QNUY1 & 1, Jsp001711, CHEBI:15349, CTK0H7179, NSC7601, MolPort-001-779-719, N-(propan-2-ylidene)hydroxylamine, NSC-7601, ANW-18957, AR-1E5152, ZINC05442063, AKOS005068118, AM90369, LS-2096, MCULE-3243100216, MP-2107, RP18316, RTR-003904, AJ-54116, AK105880, AN-43575, CJ-12625, KB-47080, AB1004364, DB-062562, ST2413699, TR-003904, A0065, FT-0621800, X9685, EN300-31960, C01995, 77336-EP2275407A1, 77336-EP2301918A1, 77336-EP2308831A1, 4-01-00-03202 (Beilstein Handbook Reference), A805635, 3B4-3750, InChI=1/C3H7NO/c1-3(2)4-5/h5H,1-2H, S14-1438

Removed Synonyms

actone oxime, acetoxime, 2-(14)C-labeled, CID67180, C035911, 80433-98-3

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