Acetic Acid → Cyclooctanone

HRID 1745877Notes

Reaction equation

HRID 1745877 reaction equation
[CH2:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:9]N1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)S1(=O)=O.[C:22]([OH:25])(=O)[CH3:23]>>[C:1]1(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:20]1([OH:21])[CH2:19][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:22]1.[C:22]1(=[O:25])[CH2:23][CH2:6][CH2:5][CH2:4][C:3](=[O:9])[CH2:2][CH2:1]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9266Cyclooctane2×HCID 10465358HCID 10465358, compound

Product 3

HCID 10403CyclooctanoneYield 19%HCID 12766CyclooctanolYield 8%HCID 5216841,4-CyclooctanedioneYield 2%

Procedure

To 27.5 ml of acetic acid were added to 336 mg (3.0 mmol) of cyclooctane, 60 mg (0.3 mmol) of N-hydroxysaccharin and 3.7 mg (0.015 mmol) of Co(OAc)2.4H2O. The resultant mixture was stirred under an oxygen atmosphere at a temperature of 50° C. for 9 hours. The products in the reaction mixture were analysed by gas chromatography, with cyclooctane being transformed, with a conversion of 43.5%, into cyclooctanone (selectivity 43.5%, yield 19%), cyclooctanol (selectivity 18%, yield 8%), 1,4-cyclooctanedione (selectivity 4.5%, yield 2%) and octanediacid (selectivity 23%, yield 10%).

Sources & evidence

ORD record
ord-cf40a610aabf4c88a399cd8f7f629e73
Source dataset
uspto-grants-2006_03
Patent number
US07019175B2

Reaction notes

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