Cycloheptane → Cycloheptyl Acetate

HRID 1885060Notes

Reaction equation

HRID 1885060 reaction equation
C1CCCCCC1.N([O:10][C:11](C)(C)[CH3:12])=O.ON1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2C1=O.C1(=NO)CCCCCC1.[N+](C1CCCCCC1)([O-])=O.C1(=O)CCCCCC1>C(O)(=O)C>[C:11]([O:21][CH:20]1[CH2:18][CH2:25][CH2:24][CH2:23][CH2:22][CH2:19]1)(=[O:10])[CH3:12]

Participants

8

Reactant 6

HCID 9265CycloheptaneHCID 10400CycloheptanoneHCID 10665N-HydroxyphthalimideHCID 10906Tert-Butyl nitriteHCID 137457Cycloheptanone OximeHCID 4189425Nitrocycloheptane

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), 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 21%, 3%, 7%, and less than 1%, respectively.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-ca31c14404d24d80a05b58904fb18e92
Source dataset
uspto-grants-2004_07
Patent number
US06768023B2

Reaction notes

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