(Trifluoromethyl)benzene → Cyclooctanone

HRID 1745881Notes

Reaction equation

HRID 1745881 reaction equation
F[C:2](F)(F)C1C=CC=CC=1.[CH2:11]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[OH:19]N1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)S1(=O)=O>>[C:11]1(=[O:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[CH:30]1([OH:31])[CH2:29][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:2]1

Participants

5

Reactant 3

HCID 7368(Trifluoromethyl)benzeneHCID 9266Cyclooctane2×HCID 10465358HCID 10465358, compound

Product 2

HCID 10403CyclooctanoneYield 16.5%HCID 12766CyclooctanolYield 6.5%

Procedure

To 9 ml of trifluorotoluene was added 336 mg (3.0 mmol) of cyclooctane, 60 mg (0.3 mmol) of N-hydroxysaccharin and 5.3 mg (0.015 mmol) of acetylacetonatocobalt Co(acac)3. The resultant mixture was stirred under an oxygen atmosphere at a temperature of 100° C. for 1.5 hours. The products in the reaction mixture were analysed by gas chromatography, with cyclooctane being transformed, with a conversion of 30%, into cyclooctanone (selectivity 54.5%, yield 16.5%), cyclooctanol (selectivity 22%, yield 6.5%) and octanediacid (selectivity 22%, yield 6.5%).

Sources & evidence

ORD record
ord-eb9187b75240451aaa30eddaafcf7b43
Source dataset
uspto-grants-2006_03
Patent number
US07019175B2

Reaction notes

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