Acetic Acid → Cyclododecanone

HRID 1745873Notes

Reaction equation

HRID 1745873 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:26]([OH:29])(=[O:28])[CH3:27]>>[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.[C:26]([O:29][CH: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)(=[O:28])[CH3:27]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9268Cyclododecane2×HCID 10465358HCID 10465358, compound

Product 3

HCID 13246CyclododecanoneYield 20%HCID 15595CyclododecanolYield 3.5%HCID 80353Cyclododecanol, 1-acetateYield 1.5%

Procedure

To 7.5 ml of acetic acid 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 100° C. for 6 hours. The products in the reaction mixture were analysed by gas chromatography, and according to this analysis, cyclododecane was transformed, with a conversion of 64%, into cyclododecanone (selectivity 31%, yield 20%) and cyclododecanol (selectivity 5.5%, yield 3.5%) and cyclododecyl acetate (selectivity 2%, yield 1.5%).

Sources & evidence

ORD record
ord-e31e8d50a5dd4d6487064f4ad3e2685d
Source dataset
uspto-grants-2006_03
Patent number
US07019175B2

Reaction notes

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