Cyclododecane → Cyclododecanone

HRID 1745874Notes

Reaction equation

HRID 1745874 reaction equation
[CH2:1]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:13]N1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)S1(=O)=O>C(#N)C>[C:1]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:24]1([OH:25])[CH2:23][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:11][CH2:12][CH2:1][CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 9268Cyclododecane2×HCID 10465358HCID 10465358, compound

Product 2

HCID 13246CyclododecanoneYield 9.5%HCID 15595CyclododecanolYield 4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 7.5 ml of acetonitrile were added 504 mg (3.0 mmol) of cyclododecane, 60 mg (0.3 mmol) of N-hydroxysaccharin and 3.9 mg (0.015 mmol) of acetylacetonatocobalt Co(acac)2. The resultant mixture was stirred under an oxygen atmosphere at a temperature of 85° C. for 22 hours. The products in the reaction mixture were analysed by gas chromatography, with cyclododecane being transformed, with a conversion of 28%, into cyclododecanone (selectivity 34.5%, yield 9.5%) and cyclododecanol (selectivity 14%, yield 4%).

Sources & evidence

ORD record
ord-d57bf9f42c0b454788c8c4cf6b1b3ebb
Source dataset
uspto-grants-2006_03
Patent number
US07019175B2

Reaction notes

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