Butanedione → HCID 178465753, compound

HRID 1369189Notes

Reaction equation

HRID 1369189 reaction equation
[CH2:1]1[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[C:11]([C:14]([CH3:16])=[O:15])([CH3:13])=[O:12].ON1[C:22](=O)[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28].[O:29]=O>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(O)(=O)C>[C:11]([C@@:5]12[CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[CH2:1][CH2:2][CH2:3][CH2:4]2)(=[O:12])[CH3:13].[OH:15][C@@:14]12[CH2:16][CH2:25][CH2:26][CH2:27][C@@H:20]1[CH2:21][CH2:22][CH2:13][CH2:11]2.[OH:12][C@@:11]12[CH2:3][CH2:2][CH2:1][CH2:10][C@:14]1([OH:15])[CH2:16][CH2:20][CH2:19][CH2:13]2.[C:19]1(=[O:28])[CH2:20][CH2:27][CH2:26][CH2:25][C:24](=[O:29])[CH2:21][CH2:22][CH2:13][CH2:11]1

Participants

10

Reactant 4

HCID 650ButanedioneHCID 977OxygenHCID 10665N-HydroxyphthalimideHCID 178420443HCID 178420443, compound

Product 4

HCID 266998Cyclodecane-1,6-dioneYield 10%HCID 178465753HCID 178465753, compoundYield 24%HCID 178514846HCID 178514846, compoundYield 22%HCID 178514847HCID 178514847, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3 mmol of cis-decalin, 18 mmol of biacetyl, 0.3 mmol of N-hydroxyphthalimide, 0.015 mmol of cobalt(II) acetate, and 3 ml of acetic acid was stirred at 75° C. in an oxygen atmosphere (1 atm) for 8 hours. A gas chromatographic analysis of products in a reaction mixture found that 4a-acetyl-cis-decalin (yield: 24%), 4a-hydroxy-cis-decalin (yield: 4%), 4a,8a-dihydroxy-cis-decalin (yield: 22%), 1,6-cyclodecanedione (yield: 10%), and 4a-acetyl-8a-hydroxy-cis-decalin (yield: 5%) were formed with a conversion rate from cis-decalin of 67%.

Sources & evidence

ORD record
ord-b600fc714c684b53a0f50d71f748aafa
Source dataset
uspto-grants-2003_06
Patent number
US06576787B1

Reaction notes

Loading…