Ethyl chrysanthemate → Chrysanthemic Acid

HRID 236432

Reaktionsgleichung

Reaktionsgleichung von HRID 236432
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]

Komponenten

4

Edukt 2

HCID 7334Ethyl chrysanthemateHCID 25134Boron tribromide

Produkt 1

HCID 2743Chrysanthemic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

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%.

Aufarbeitung

  1. stirringstirred for 4 hours

Quellen und Nachweise

ORD-Eintrag
ord-eb4a9b79b5dd49b5ab74a0e97bc615b0
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04644080

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