(Trifluoromethyl)benzene → Cyclododecanone

HRID 1745875Notes

Reaction equation

HRID 1745875 reaction equation
FC(F)(F)[C:3]1[CH:8]=[CH:7]C=[CH:5][CH:4]=1.[CH2:11]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[OH:23]N1[C:34](=[O:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)S1(=O)=O>>[C:11]1(=[O:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[CH:34]1([OH:35])[CH2:33][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:7][CH2:8][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 7368(Trifluoromethyl)benzeneHCID 9268Cyclododecane2×HCID 10465358HCID 10465358, compound

Product 2

HCID 13246CyclododecanoneYield 22%HCID 15595CyclododecanolYield 5.5%

Procedure

To 9 ml of trifluorotoluene was added 504 mg (3.0 mmol) of cyclododecane, 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 4 hours. The products in the reaction mixture were analysed by gas chromatography, with cyclododecane being transformed, with a conversion of 34.5%, into cyclododecanone (selectivity 64%, yield 22%), cyclododecanol (selectivity 16.5%, yield 5.5%) and dodecanediacid (selectivity 5%, yield 2%).

Sources & evidence

ORD record
ord-856d7c899b884018b6c7c09d30c653c6
Source dataset
uspto-grants-2006_03
Patent number
US07019175B2

Reaction notes

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