Ethyl chrysanthemate → Chrysanthemic Acid

HRID 1198855Notes

Reaction equation

HRID 1198855 reaction equation
CC[O:3][C:4]([CH:6]1[C:8]([CH3:10])([CH3:9])[CH:7]1[CH:11]=[C:12]([CH3:14])[CH3:13])=[O:5].B(Br)(Br)Br>C1(C)C=CC=CC=1>[CH3:13][C:12]([CH3:14])=[CH:11][CH:7]1[C:8]([CH3:9])([CH3:10])[CH:6]1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 7334Ethyl chrysanthemateHCID 25134Boron tribromide

Product 1

HCID 2743Chrysanthemic AcidYield 112%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the same levo-rotatory ethyl chrysanthemate (10 g) as used in Example 12 in toluene (90 g) was added boron tribromide (0.18 g) at room temperature under a nitrogen atmosphere. Irradiation with a high pressure mercury lamp (110 W) was made for 30 minutes. After the reaction was over, similar after-treatment as in Example 12 was applied to obtain chrysanthemic acid (9.6 g). The optical isomer ratio of the product was (+)-cis, 4.0%; (-)-cis, 2.6%; (+)-trans, 42.5%; and (-)-trans, 50.9%.

Workup

  1. customIrradiation with a high pressure mercury lamp (110 W)

Sources & evidence

ORD record
ord-d0298c16340149b4af13f50a16b56d6a
Source dataset
uspto-grants-1990_02
Patent number
US04898655

Reaction notes

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