1-Naphthaldehyde → 2-(1-Naphthylmethylene)glutaric acid

HRID 1768597

Reaktionsgleichung

Reaktionsgleichung von HRID 1768597
[H-].[Na+].[C:3]([O:12]C)(=[O:11])[CH2:4][CH2:5][CH2:6][C:7]([O:9]C)=[O:8].[C:14]1([CH:24]=O)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>CO>[C:14]1([CH:24]=[C:4]([CH2:5][CH2:6][C:7]([OH:9])=[O:8])[C:3]([OH:12])=[O:11])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 61951-NaphthaldehydeHCID 14242Dimethyl GlutarateHCID 14798Sodium HydroxideHCID 24758Sodium hydride

Produkt 1

HCID 539440592-(1-Naphthylmethylene)glutaric acidAusbeute 42,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

8.17 g (0.19 mole) of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling, to a solution of 25 g (0.16 mole) of dimethyl glutarate and 23.4 g (0.16 mole) of 1-naphthaldehyde dissolved in 200 ml of anhydrous methanol. The mixture was heated under reflux for 30 minutes, after which 190 ml (0.19 mole) of a 1N aqueous solution of sodium hydroxide were added to it, and the mixture was again heated under reflux for 1 hour. The solvent was removed by distillation under reduced pressure, and the resulting residue was mixed with water and washed with diethyl ether. The aqueous layer was acidified and then extracted with diethyl ether. The ethereal layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and then diisopropyl ether was added to the residue to precipitate crystals, which were collected by filtration to give 18.5 g of 2-(1 -naphthylmethylene)glutaric acid.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturethe mixture was again heated
  4. temperatureunder reflux for 1 hour
  5. customThe solvent was removed by distillation under reduced pressure
  6. additionthe resulting residue was mixed with water
  7. washwashed with diethyl ether
  8. extractionextracted with diethyl ether
  9. washThe ethereal layer was washed with a saturated aqueous solution of sodium chloride
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. additiondiisopropyl ether was added to the residue
  13. customto precipitate crystals, which
  14. filtrationwere collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-3071136b52fb45d998ca0e2d2f24ddbb
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05378690

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