Ethyl chrysanthemate → Chrysanthemic Acid

HRID 236432

Reaction equation

HRID 236432 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>O1CCOCC1>[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 Acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
15 °C

Procedure

In a 50 ml flask, there were charged ethyl chrysanthemate (composition: (+)-cis, 2.5%; (-)-cis, 16.8%; (+)-trans, 12.3%; (-)-trans, 68.4%) (2.0 g) and dioxane (18.0 g) under nitrogen. Boron tribromide (0.26 g) was added thereto at 15° C. with stirring and stirred for 4 hours. Then a small amount of the reaction mixture was hydrolyzed to obtain chrysanthemic acid. The composition of the optical isomers in the product was determined by the same method as described in EXAMPLE 1. The result was as follows: (+)-cis, 2.4%; (-)-cis, 2.6%; (+)-trans, 46.2%; (-)-trans, 48.8%.

Workup

  1. stirringstirred for 4 hours

Sources & evidence

ORD record
ord-eb4a9b79b5dd49b5ab74a0e97bc615b0
Source dataset
uspto-grants-1987_02
Patent number
US04644080

Linked notes

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