Cyclopentanone → Cyclopentanol, acetate

HRID 1885056Notes

Reaction equation

HRID 1885056 reaction equation
N([O:3][C:4](C)(C)[CH3:5])=O.ON1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17]C=C2C1=O.C1(=NO)CCCC1.[N+](C1CCCC1)([O-])=O.C1(=O)CCCC1>C(O)(=O)C.C1CCCC1>[C:4]([O:14][CH:13]1[CH2:12][CH2:15][CH2:16][CH2:17]1)(=[O:3])[CH3:5]

Participants

8

Reactant 5

HCID 8452CyclopentanoneHCID 10665N-HydroxyphthalimideHCID 10906Tert-Butyl nitriteHCID 14500Cyclopentanone, oximeHCID 75714Nitrocyclopentane

Product 1

HCID 70273Cyclopentanol, acetate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 9253CyclopentaneSolvent

Conditions

Temperature
80 °C

Procedure

Cyclopentane (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 cyclopentanone oxime, nitrocyclopentane, cyclopentanone, and cyclopentyl acetate were formed in yields of 4%, 2%, 3%, and less than 1%, respectively.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-346888ec32b94910b8e7ef670780cedf
Source dataset
uspto-grants-2004_07
Patent number
US06768023B2

Reaction notes

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