Acetone → Diethyl 1,4-bis(propyloxy)-2,3-naphthalenedicarboxylate

HRID 889478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889478
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][CH3:32].[CH3:33][C:34]([CH3:36])=O>C1(C)C=CC=CC=1>[CH2:30]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:33][CH2:34][CH3:36])=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:31][CH3:32]

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 431092,3-Diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate

Produkt 1

HCID 58017588Diethyl 1,4-bis(propyloxy)-2,3-naphthalenedicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate* (11 g, 36.1 mmol) was dissolved in acetone (180 ml) and potassium carbonate (24.9 g, 180.5 mmol) added and stirred. 1-Bromopropane (13.1 ml, 144.4 mmol) was added and the reaction mixture was heated at reflux (60° C.) overnight under argon. The reaction was cooled to room temperature and the inorganic solid filtered off. The solvent was evaporated to give an orange brown oil. The residue was taken up in toluene and washed with 5% potassium hydroxide solution, brine and dried over magnesium sulphate. Solvent was removed under vacuum to give a brown oil which was purified by chromatography on silica gel eluting with, 10% ethyl acetate in hexane. The clean fractions were evaporated to give the title compound as yellow oil (11.45 g, 29.5 mmol).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationthe inorganic solid filtered off
  4. customThe solvent was evaporated
  5. customto give an orange brown oil
  6. washwashed with 5% potassium hydroxide solution, brine
  7. dry with materialdried over magnesium sulphate
  8. customSolvent was removed under vacuum
  9. customto give a brown oil which
  10. customwas purified by chromatography on silica gel eluting with, 10% ethyl acetate in hexane
  11. customThe clean fractions were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c7515423828d435997a20d59a2e8f12c
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252833B2

Notizen zur Reaktion

Wird geladen…