Ethyl chrysanthemate → chrysanthemic acid d-trans-form

HRID 267572

Reaktionsgleichung

Reaktionsgleichung von HRID 267572
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].[OH-].[Na+]>C(O)C>[CH3:13][C:12]([CH3:14])=[CH:11][C@H:7]1[C:8]([CH3:9])([CH3:10])[C@@H:6]1[C:4]([OH:5])=[O:3]

Komponenten

4

Edukt 2

HCID 7334Ethyl chrysanthemateHCID 14798Sodium Hydroxide

Produkt 1

HCID 16747chrysanthemic acid d-trans-formAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In a 500 ml volume four-necked flask, there were charged ethyl chrysanthemate consisting of 33.6 % of the cis-isomer and 66.4 % of the trans-isomer (100 g; trans-isomer, 0.34 mol), a 25 % aqueous solution of sodium hydroxide (30 g; NaOH, 0.19 mol) and ethanol (50 g), and the mixture was stirred at 60°C for 5 hours as in Example 1. After removing ethanol by distillation, the reaction mixture was treated as in Example 1 to give trans-chrysanthemic acid (28.7 g; trans-isomer, 90.0 %) and unreacted ethyl chrysanthemate (64.0 g; cis/trans = 53.8/46.2).

Aufarbeitung

  1. customAfter removing ethanol
  2. distillationby distillation
  3. additionthe reaction mixture was treated as in Example 1

Quellen und Nachweise

ORD-Eintrag
ord-242b87e83df847c79631511ae2559167
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03943167

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