Dimethylformamide → 5-Methoxy-3-stilbene carboxylic acid methyl ester

HRID 261347

Reaktionsgleichung

Reaktionsgleichung von HRID 261347
[H-].[Na+].[CH2:3](P(=O)(OCC)OCC)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:18][O:19][C:20](=[O:31])[C:21]1[CH2:22][C:23]([O:29][CH3:30])([CH:26]=[CH:27][CH:28]=1)C=O.[CH3:32]N(C)C=O>>[CH3:18][O:19][C:20]([C:21]1[CH:28]=[C:27]([CH:32]=[CH:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:26]=[C:23]([O:29][CH3:30])[CH:22]=1)=[O:31]

Komponenten

5

Edukt 4

HCID 6228Dimethylformamide2×HCID 14122Diethyl benzylphosphonateHCID 24758Sodium hydrideHCID 86736055HCID 86736055, Verbindung

Produkt 1

HCID 545477545-Methoxy-3-stilbene carboxylic acid methyl ester

Versuchsvorschrift

To a slurry of 1.0 mole of sodium hydride in one liter of N,N-dimethylformamide is added 1.0 mole of diethyl benzylphosphonate. The reaction mixture is stirred for one hour and then a solution of 1.0 mole of 3-methoxyisophthalaldehydic acid methyl ester in a minimal amount of dimethylformamide is added. The reaction mixture is stirred for several hours and is then added to ether-water. The ether extract is washed several times with water, dried over magnesium sulfate and evaporated to a residue. The residue is purified via crystallization from hexane to yield 5-methoxy-3-stilbene carboxylic acid methyl ester. The free acid is obtained by refluxing a solution of 1.0 mole of the methyl ester in one liter in 1 N methanolic sodium hydroxide for 4-5 hours. The reaction mixture is evaporated to a residue which is added to ethyl acetate. The ethyl acetate solution is extracted with several portions of water. The combined aqueous extract is neutralized with 1 N hydrochloric acid and extracted with several portions of ethyl acetate. This organic extract is dried over magnesium sulfate and evaporated to a residue. The residue is purified by crystallization from hexane to yield 5-methoxy-3-stilbene carboxylic acid.

Aufarbeitung

  1. stirringThe reaction mixture is stirred for several hours
  2. extractionThe ether extract
  3. washis washed several times with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to a residue
  6. customThe residue is purified via crystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-4fc320218f8640cba7b1a1fe4fed7207
Quelldatensatz
uspto-grants-1979_08
Patentnummer
US04165323

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