Cyclooctane → Cyclooctanone

HRID 1885063Notes

Reaction equation

HRID 1885063 reaction equation
C1CCCCCCC1.N(OC(C)(C)C)=O.ON1[C:21](=O)[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27].C1(=NO)CCCCCCC1.[N+](C1CCCCCCC1)([O-])=O>C(O)(=O)C>[C:18]1(=[O:27])[CH2:19][CH2:26][CH2:25][CH2:24][CH2:23][CH2:20][CH2:21]1

Participants

7

Reactant 5

HCID 9266CyclooctaneHCID 10665N-HydroxyphthalimideHCID 10906Tert-Butyl nitriteHCID 136841Cyclooctanone, oximeHCID 11240629HCID 11240629, compound

Product 1

HCID 10403Cyclooctanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Cyclooctane (2 ml), t-butyl nitrite (1 mmol), 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 cyclooctanone oxime, nitrocyclooctane, and cyclooctanone were formed in yields of 64%, 4%, and 2%, respectively.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-144856ada1af47038145d49fe39c6b3b
Source dataset
uspto-grants-2004_07
Patent number
US06768023B2

Reaction notes

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