2,3-Dimethoxy-1,4-naphthoquinone → HCID 20403098, Verbindung

HRID 2164719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2164719
[Al+3].[Cl-].[Cl-].[Cl-].CO[C:7]1[C:8](=[O:20])[C:9]2[C:14]([C:15](=[O:19])[C:16]=1[O:17][CH3:18])=[CH:13][CH:12]=[CH:11][CH:10]=2.[NH4+].[Cl-].[CH2:23]1[CH2:27]O[CH2:25][CH2:24]1>[Cl-].[Cl-].[Zn+2]>[CH3:18][O:17][C:16]1[C:15](=[O:19])[C:14]2[C:9]([C:8](=[O:20])[C:7]=1[CH2:25][CH2:24][CH2:23][CH2:27][CH2:9][CH2:8][CH2:7][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12])=[CH:10][CH:11]=[CH:12][CH:13]=2

Komponenten

6

Edukt 4

HCID 31362,3-Dimethoxy-1,4-naphthoquinoneHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 20403098HCID 20403098, VerbindungAusbeute 2,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3007855ZincchlorideKatalysator

Versuchsvorschrift

To 0.216 g (1.62 mmoles) of AlCl3 in 50 mL of THF was added 7.0 g (0.697 mmoles/g in THF, 4.88 mmoles) of dodecyl MgBr. This mixture was added dropwise to 1.27 g (9.34 mmoles) of ZnCl2 and 1.00 g (4.67 mmoles) of 2,3-dimethoxy-1,4-naphthoquinone in 50 mL of THF. The mixture was stirred overnight, poured into 100 mL of NH4Cl solution, extracted with 3×50 mL of ether, dried over MgSO4, filtered, and solvent was removed by rotary evaporation. The residue was chromatographed on silica gel eluted with toluene. Thus, 0.034 g (0.096 mmoles, 2.1%) of 2-methoxy-3-dodecylnaphthoquinone was obtained.

Aufarbeitung

  1. extractionextracted with 3×50 mL of ether
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customsolvent was removed by rotary evaporation
  5. customThe residue was chromatographed on silica gel
  6. washeluted with toluene

Quellen und Nachweise

ORD-Eintrag
ord-581aba924ef24389b604445cff161a5b
Quelldatensatz
uspto-grants-1985_03
Patentnummer
US04507241

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