Cyanoacetic acid → HCID 53797226, Verbindung

HRID 439568

Reaktionsgleichung

Reaktionsgleichung von HRID 439568
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)=O.[C:14]([CH2:16][C:17]([OH:19])=[O:18])#[N:15].C([O-])(=O)C.[NH4+].[OH-].[Na+]>C1C=CC=CC=1.O.C(Cl)(Cl)Cl.C(O)(=O)C>[C:14]([CH:16]([CH:2]([CH3:1])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)[C:17]([OH:19])=[O:18])#[N:15]

Komponenten

9

Edukt 4

HCID 9740Cyanoacetic acidHCID 143283,4-Dimethoxyphenyl methyl ketoneHCID 14798Sodium HydroxideHCID 517165Ammonium Acetate2×

Produkt 1

HCID 53797226HCID 53797226, VerbindungAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 3, 4-dimethoxyacetophenone (5.68 g, 31.53 mmol) and cyanoacetic acid (2.95 g, 34.68 mmol) in benzene were added acetic acid (1.9 ml) and ammonium acetate (150 mg), and the resultant mixture was refluxed with Dean Stark's dehydrating apparatus for 13 hours while adding ammonium acetate (130 mg) every 4 hours. The mixture was mixed with chloroform (200 ml), 2N aqueous sodium hydroxide solution (100 ml) and water (200 ml), stirred well and the aqueous layer was separated. The aqueous layer was acidified with dilute hydrochloric acid, and the resulting precipitate was filtered off. The residue was washed with diethyl ether to give a carboxylic acid, 2-cyano-3-methyl-3-(3, 4-dimethoxyphenyl) propionic acid (2.25 g, 29%).

Aufarbeitung

  1. customfor 13 hours
  2. customthe aqueous layer was separated
  3. filtrationthe resulting precipitate was filtered off
  4. washThe residue was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f0b4f5986f8848e384f73298b1fa4404
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05514711

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