Cycloheptane → Cycloheptyl Acetate

HRID 1885061Notes

Reaction equation

HRID 1885061 reaction equation
C1CCCCCC1.N([O:10][C:11](C)(C)[CH3:12])=O.Cl[C:16]1[CH:17]=[C:18]2[C:23](=[O:24])N(O)C(=O)[C:19]2=[CH:26][CH:27]=1.C1(=NO)CCCCCC1.[N+](C1CCCCCC1)([O-])=O.C1(=O)CCCCCC1>C(O)(=O)C>[C:11]([O:24][CH:23]1[CH2:17][CH2:16][CH2:27][CH2:26][CH2:19][CH2:18]1)(=[O:10])[CH3:12]

Participants

8

Reactant 6

HCID 9265CycloheptaneHCID 10400CycloheptanoneHCID 10906Tert-Butyl nitriteHCID 137457Cycloheptanone OximeHCID 4189425NitrocycloheptaneHCID 221784105-Chloro-2-hydroxy-1H-isoindole-1,3(2H)-dione

Product 1

HCID 11423718Cycloheptyl Acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Cycloheptane (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 cycloheptanone oxime, nitrocycloheptane, cycloheptanone, and cycloheptyl acetate were formed in yields of 16%, 4%, 6%, and less than 1%, respectively.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-0dc4d9e6cd524ed29fa905cde8c09270
Source dataset
uspto-grants-2004_07
Patent number
US06768023B2

Reaction notes

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