Azobisisobutyronitrile → Chrysanthemic Acid

HRID 620452

Reaction equation

HRID 620452 reaction equation
[CH3:1][C:2]([CH3:12])=[CH:3][C@H:4]1[C:6]([CH3:8])([CH3:7])[C@H:5]1[C:9]([OH:11])=[O:10].N(C(C)(C)C#N)=NC(C)(C)C#N.BrBr>C1(C)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]([CH3:12])=[CH:3][CH:4]1[C:6]([CH3:7])([CH3:8])[CH:5]1[C:9]([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 20755Chrysanthemic acid, cis-(-)-HCID 24408Bromine

Product 1

HCID 2743Chrysanthemic AcidYield 90.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

500 mg of (-)-cis-chrysanthemic acid was dissolved in 10 ml of toluene, followed by adding 20 mg of azobisisobutyronitrile. Thereto was added dropwise a solution of bromine (19 mg) in carbon tetrachloride at 80° C. over a period of 10 minutes with stirring. After 15 minutes, the reaction mixture was subjected to a treatment similar to Example 1 to obtain 452 mg of chrysanthemic acid. The optical isomer ratio was as follows: (+)-cis, 3.3%; (-)-cis, 3.2%; (+)-trans, 47.0%; and (-)-trans, 46.5%.

Sources & evidence

ORD record
ord-8f2f56d3eeb5432896c518c1e5fd3ef8
Source dataset
uspto-grants-1989_04
Patent number
US04820864

Linked notes

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