Sodium Hydroxide → 2-[1-(2,4-Dimethoxyphenyl)hexyl]malonic acid

HRID 1637484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637484
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[CH:13]([CH:19]([C:25]([O:27]CC)=[O:26])[C:20]([O:22]CC)=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>O.C(O)C>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[CH:13]([CH:19]([C:20]([OH:22])=[O:21])[C:25]([OH:27])=[O:26])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 19348766Diethyl 2-[1-(2,4-dimethoxyphenyl)hexyl]malonate

Produkt 1

HCID 193484652-[1-(2,4-Dimethoxyphenyl)hexyl]malonic acidAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 4.40 g (110 mmol) of sodium hydroxide in 14 ml of water was added to a solution of 8.37 g (22.0 mmol) of diethyl 2-[1-(2,4-dimethoxyphenyl)hexyl]malonate (prepared as described in Preparation 2) in 50 ml of ethanol, and the resulting mixture was heated under reflux for 2.5 hours. At the end of this time, the reaction mixture was allowed to cool to room temperature, after which it was freed from ethanol by evaporation under reduced pressure. The resulting residue was acidified with concentrated hydrochloric acid and then extracted with ethyl acetate. The extract was washed with water and then with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, to give 6.57 g of the title compound as a foam-like substance.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. customafter which it was freed from ethanol by evaporation under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialwith a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-163cf50466ef43d89b512ad625698dd6
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06040339

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