Azobisisobutyronitrile → Chrysanthemic Acid

HRID 620454Notes

Reaction equation

HRID 620454 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 95.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

2.0 g of cis-chrysanthemic acid and 23 mg of azobisisobutyronitrile were dissolved in 20 ml of toluene and thereto was added dropwise a solution of bromine (21 mg) in carbon tetrachloride with stirring at 80° C. over a period of 20 minutes. Thereafter, a treatment similar to Example 1 was carried out to obtain 1.91 g of chrysanthemic acid. Gas chromatographic assay thereof showed the composition: cis, 9.8% and trans, 90.2%.

Sources & evidence

ORD record
ord-37eecdbf47564be0a4584111c6340093
Source dataset
uspto-grants-1989_04
Patent number
US04820864

Reaction notes

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