Oxygen → Cyclooctene-3-one

HRID 618983

Reaction equation

HRID 618983 reaction equation
C1CCCCCCC=1.ON1[C:14](=O)[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20].O=O>C(#N)C>[C:11]1(=[O:20])[CH2:14][CH2:13][CH2:16][CH2:17][CH2:18][CH:19]=[CH:12]1.[CH:11]1([OH:20])[CH2:14][CH2:13][CH2:16][CH2:17][CH2:18][CH:19]=[CH:12]1

Participants

6

Reactant 3

HCID 977OxygenHCID 10665N-HydroxyphthalimideHCID 136091-Cyclooctene2×

Product 2

HCID 983282-Cycloocten-1-olYield 15%HCID 137176Cyclooctene-3-oneYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.10 grams (10 millimoles) of cyclooctene, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide, 0.021 gram (0.06 millimole) of acetylacetonatocobalt Co(AA)2 and 25 milliliters of acetonitrile was stirred in an oxygen atmosphere at a temperature of 100° C. for 6 hours. The product in the reaction mixture was analyzed with gas chromatography. Cyclooctene was transformed, with a transformation rate of 95%, into 2-cycloocten-1-one (cyclooctene-based selectivity 82%, yield 78%) and 2-cycloocten-1-ol (cyclooctene-based selectivity 16%, yield 15%).

Sources & evidence

ORD record
ord-5629545e6ea04bcdaa5d4c52c2efc6e4
Source dataset
uspto-grants-1999_09
Patent number
US05958821

Linked notes

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