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

HRID 1198857Notes

Reaction equation

HRID 1198857 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].P(Br)(Br)Br>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 24614Phosphorus tribromide

Product 1

HCID 2743Chrysanthemic AcidYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of cis chrysanthemic acid (1.0 g) in toluene (9 g) was added phosphorus tribromide (0.11 g) at room temperature under a nitrogen atmosphere. Irradiation with a xenon lamp (500 W, Pyrex glass filter) was made for 30 minutes under stirring. After the irradiation was over, similar after-treatment as in Example 1 was applied to obtain chrysanthemic acid (0.90 g). The isomer ratio of the product was: cis, 10.0%; and trans, 90.0%.

Workup

  1. customIrradiation with a xenon lamp
  2. filtration(500 W, Pyrex glass filter)
  3. customAfter the irradiation

Sources & evidence

ORD record
ord-9944d14ec7c04c9781ccb8c4350716bb
Source dataset
uspto-grants-1990_02
Patent number
US04898655

Reaction notes

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