Synthesis of cyclohexanone oxime

Preparation of cyclohexanone oxime (cyclohexanone, oxime; antioxidant D; n-cyclohexylidenehydroxylamine)

Preparation of cyclohexanone oxime (cyclohexanone, oxime; antioxidant D; n-cyclohexylidenehydroxylamine)

Preparation of cyclohexanone oxime (cyclohexanone, oxime; antioxidant D; n-cyclohexylidenehydroxylamine)

2.5 g of hydroxylamine hydrochloride and 4 g of crystallised sodium acetate are dissolved in 10 ml of water. The solution is warmed to about 40° C and 2.5 g of cyclohexanone are added. The reaction mixture is heated and stirred vigorously and after few minutes the cyclohexanone oxime separates as a crystalline solid. The reaction mixture is cooled in ice, filtered, washed with a little cold water. The product is purified by crystallization from light petroleum (b.p. 60-80° C), yielding 2.5 g of pure  cyclohexanone oxime, which melts at 90° C.

A text book of practical organic chemistry, by A. I. Vogel, 343, 1974

IUPAC Name

N-cyclohexylidenehydroxylamine

InChI

InChI=1S/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2

InChI Key

VEZUQRBDRNJBJY-UHFFFAOYSA-N

Canonical SMILES

C1CCC(=NO)CC1

MeSH Synonyms

cyclohexanone oxime

Depositor-Supplied Synonyms

Cyclohexanone oxime, 100-64-1, Cyclohexanone, oxime, Antioxidant D, (HYDROXYIMINO)CYCLOHEXANE, N-cyclohexylidenehydroxylamine, NSC 6300, UNII-2U60L00CGF, CCRIS 1383, HSDB 5337, VEZUQRBDRNJBJY-UHFFFAOYSA-N, EINECS 202-874-0, BRN 1616769, AI3-07288, DSSTox_CID_1842, DSSTox_RID_76361, DSSTox_GSID_21842, CAS-100-64-1, hydroxyiminocyclohexane, Cyclo-hexanone, oxime, N-hydroxycyclohexanimine, AC1L1OXV, WLN: L6YTJ AUNQ, ACMC-1C9KD, SCHEMBL37995, KSC179O1P, C102202_ALDRICH, N-cyclohexylidene-hydroxylamine, 2U60L00CGF, ARONIS007712, CHEMBL137035, Jsp000147, CTK0H9717, NSC6300, MolPort-000-872-080, HMS1787F13, NSC-6300, Tox21_202143, Tox21_303015, ANW-14334, LS-309, SBB058381, STL069070, ZINC03860302, AKOS000121564, MCULE-4628080057, NE10113, RTR-000218, TRA0040635, NCGC00091157-01, NCGC00091157-02, NCGC00256578-01, NCGC00259692-01, AN-24559, KB-49216, M218, SC-76798, T819, DB-012726, TR-000218, FT-0624194, ST45044465, 77341-EP2275407A1, 77341-EP2292599A1, 77341-EP2301918A1, 77341-EP2301919A1, 77341-EP2308831A1, 4-07-00-00021 (Beilstein Handbook Reference), A800249, I14-0905, T5225159, I14-21130, 3B3-036042, CYCLOHEXANONE OXIME (2-BUTANONE OXIME (96-29-7)), InChI=1/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H, 1071540-61-8, 136056-95-6, 136057-01-7

Removed Synonyms

CID7517, c0490, 1000341-04-7

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