Oxygen → 2-Cyclohexen-1-one

HRID 618982Notes

Reaction equation

HRID 618982 reaction equation
[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[OH:7]N1C(=O)[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2C1=O.[O:19]=O>C(#N)C>[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[CH:10]1([OH:19])[CH2:11][CH2:14][CH2:15][CH:16]=[CH:17]1

Participants

6

Reactant 3

HCID 977OxygenHCID 8079Cyclohexene2×HCID 10665N-Hydroxyphthalimide

Product 2

HCID 131982-Cyclohexen-1-OLYield 13%HCID 135942-Cyclohexen-1-oneYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 25 milliliters of acetonitrile were added 1.64 grams (20 millimoles) of cyclohexene, 0.26 gram (1.6 millimoles) of N-hydroxyphthalimide and 0.043 gram (0.12 millimole) of acetylacetonatocobalt Co(AA)2. The resultant mixture was stirred in an oxygen atmosphere at 100° C. for 6 hours. The products in the reaction mixture were analyzed with gas chromatography, and cyclohexene was transformed, with a transformation rate of 90%, into 2-cyclohexen-1-one (selectivity based on cyclohexene 72%, yield 65%) and 2-cyclohexen-1-ol (selectivity based on cyclohexene 14%, yield 13%).

Sources & evidence

ORD record
ord-7abe8258ea2641eb8c1d08ff97dad681
Source dataset
uspto-grants-1999_09
Patent number
US05958821

Reaction notes

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