1,2-Dimethoxyethane → 3-[(4-Methoxyphenyl)methyl]glutaric acid

HRID 27370

Reaktionsgleichung

Reaktionsgleichung von HRID 27370
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#N.[OH-:7].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17]C=O)=[CH:13][CH:12]=1.[CH2:20]([CH2:23][O:24]C)OC>O>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH:1]([CH2:20][C:23]([OH:24])=[O:7])[CH2:3][C:4]([OH:6])=[O:5])=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 9740Cyanoacetic acidHCID 14798Sodium HydroxideHCID 797824-Methoxyphenylacetaldehyde

Produkt 1

HCID 205288313-[(4-Methoxyphenyl)methyl]glutaric acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of cyanoacetic acid (3.57 g), in water (20 ml) is added a solution of sodium hydroxide (2.08 g) in water (20 ml). The solution is diluted with glyme (70 ml), 4-methoxyphenyl acetaldehyde (3.0 g) is added and the mixture is left at room temperature for 6.0 hours. The glyme is evaporated in vacuo, and the residue is mixed with 10% hydrochloric acid (200 ml) and refluxed for 6.0 hours. After cooling, the mixture is extracted with ethyl acetate. The ethyl acetate extract is washed once with brine, dried, evaporated and the residue subjected to chromatography on a column of silica gel using chloroform-ethyl acetate mixtures for elution to afford 2.2 g of 3-[(4-methoxyphenyl)methyl]glutaric acid. Crystallization from a benzene-ethyl acetate-hexane mixture gives a specimen having a melting point 109°-110° C.

Aufarbeitung

  1. additionis added
  2. customThe glyme is evaporated in vacuo
  3. additionthe residue is mixed with 10% hydrochloric acid (200 ml)
  4. temperaturerefluxed for 6.0 hours
  5. temperatureAfter cooling
  6. extractionthe mixture is extracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. washis washed once with brine
  9. customdried
  10. customevaporated
  11. washfor elution

Quellen und Nachweise

ORD-Eintrag
ord-0382624145fe452ebdea526e51f67c5a
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04221725

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