Chrysanthemic acid, cis-(-)- → Chrysanthemic Acid

HRID 1198859Notes

Reaction equation

HRID 1198859 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].[Br-].[Br-].[Br-].[Al+3]>C1(C)C=CC=CC=1>[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

4

Reactant 2

HCID 20755Chrysanthemic acid, cis-(-)-HCID 166749Bromhydrol

Product 1

HCID 2743Chrysanthemic AcidYield 98.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of cis chrysanthemic acid (2.0 g) in toluene (20 ml) was added a solution of aluminum tribromide (32 mg) in toluene (2.2 ml) at room temperature under a nitrogen atmosphere. Irradiation with a xenon lamp (500 W) was made for 10 minutes under stirring. After the irradiation was over, similar after-treatment as in Example 30 was applied to obtain chrysanthemic acid (1.97 g). The isomer ratio of the product was cis, 6.8%; and trans, 93.2%.

Workup

  1. customIrradiation with a xenon lamp (500 W)
  2. customAfter the irradiation

Sources & evidence

ORD record
ord-59c14a9b9bf242d4a9ee269406fd2730
Source dataset
uspto-grants-1990_02
Patent number
US04898655

Reaction notes

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