Acetic Acid → Cyclononanone

HRID 618980Notes

Reaction equation

HRID 618980 reaction equation
[CH2:1]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:10]N1[C:15](=O)[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].[O:22]=O.[C:24]([OH:27])(=[O:26])C>>[C:1]1(=[O:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:24]([OH:27])(=[O:26])[CH2:15][CH2:14][CH2:17][CH2:18][CH2:19][CH2:20][CH2:13][C:12]([OH:21])=[O:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 10665N-HydroxyphthalimideHCID 136143Cyclononane2×

Product 2

HCID 2266Azelaic AcidYield 42%HCID 76877CyclononanoneYield 46%

Procedure

To 25 milliliters of acetic acid were added 1.26 grams (10 millimoles) of cyclononane, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide and 0.015 gram (0.06 millimole) of Co(AA)2, and the resultant mixture was stirred in an oxygen atmosphere at a temperature of 100° C. for six hours. Products in the reaction mixture were analyzed by means of gas chromatography, which showed that cyclononane was transformed into cyclononanone (yield 46%) and azelaic acid (yield 42%) with a transformation rate of 92%.

Sources & evidence

ORD record
ord-e48ee11f00ac4e63a57d171556889521
Source dataset
uspto-grants-1999_09
Patent number
US05958821

Reaction notes

Loading…