Cyclohexanone Oxime → Cyclohexyl acetate

HRID 1885058Notes

Reaction equation

HRID 1885058 reaction equation
N([O:3][C:4](C)(C)[CH3:5])=O.ClC1C=C2C(=O)N(O)C(=O)C2=CC=1.C1(=NO)CCCCC1.[N+](C1CCCCC1)([O-])=O.[C:38]1(=[O:44])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>C(O)(=O)C.C1CCCCC1>[C:4]([O:44][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)(=[O:3])[CH3:5]

Participants

8

Reactant 5

HCID 7517Cyclohexanone OximeHCID 7967CyclohexanoneHCID 10906Tert-Butyl nitriteHCID 14285NitrocyclohexaneHCID 221784105-Chloro-2-hydroxy-1H-isoindole-1,3(2H)-dione

Product 1

HCID 12146Cyclohexyl acetate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
80 °C

Procedure

Cyclohexane (1 ml), t-butyl nitrite (1 mmol), 4-chloro-N-hydroxyphthalimide (0.2 mmol), and acetic acid (1 ml) were placed in a flask and were stirred at 80° C. in an atmosphere of argon gas (1 atm=0.101 MPa) for 20 hours. The resulting reaction mixture was analyzed to find that cyclohexanone oxime, nitrocyclohexane, cyclohexanone, and cyclohexyl acetate were formed in yields of 13%, 9%, 2%, and 2%, respectively.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-395f6cf10e5248ad952791e449d7c484
Source dataset
uspto-grants-2004_07
Patent number
US06768023B2

Reaction notes

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