Sulfuric Acid → 3,5,6-Trimethyl-2-[phenyl-(3-pyridyl)methyl]-1,4-benzoquinone

HRID 1030588

Reaktionsgleichung

Reaktionsgleichung von HRID 1030588
[C:1]1([CH:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][C:16]1[C:22]([CH3:23])=[C:21]([OH:24])[C:20]([CH3:25])=[CH:19][C:17]=1[OH:18].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>ClC(Cl)C>[CH3:25][C:20]1[C:21](=[O:24])[C:22]([CH3:23])=[C:16]([CH3:15])[C:17](=[O:18])[C:19]=1[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 12785TrimethylhydroquinoneHCID 234839Phenyl(pyridin-3-yl)methanolHCID 516892Sodium Bicarbonate

Produkt 1

HCID 142777673,5,6-Trimethyl-2-[phenyl-(3-pyridyl)methyl]-1,4-benzoquinoneAusbeute 72,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 1.0 g (5.4 mmol) of phenyl-(3-pyridyl) methanol and 823 mg (5.4 mmol) of 2,3,5-trimethylhydroquinone in 15 ml of dichloroethane, 0.5 ml (9.4 mmol) of concentrated sulfuric acid was added, and refluxed by heating for 2 hours. The reaction mixture was made weakly alkaline with a saturated aqueous solution of sodium hydrogen carbonate, from which the organic phase was separated while the aqueous phase was extracted with chloroform and the extract was combined with the organic phase. The organic phase was washed with water, dried, and oxidized with air, from which the solvent was evaporated off. The residue was purified with silica gel column chromatography (isopropyl ether-ethyl acetate (1:1)), to give 1.25 g (72.7%) of 3,5,6-trimethyl-2[phenyl-(3-pyridyl)methyl]-1,4-benzoquinone. The physical data are shown in Table 1.

Aufarbeitung

  1. temperaturerefluxed
  2. temperatureby heating for 2 hours
  3. customfrom which the organic phase was separated while the aqueous phase
  4. extractionwas extracted with chloroform
  5. washThe organic phase was washed with water
  6. customdried
  7. customwas evaporated off
  8. customThe residue was purified with silica gel column chromatography (isopropyl ether-ethyl acetate (1:1))

Quellen und Nachweise

ORD-Eintrag
ord-f56caf5291614e4f83f85a40828f292e
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106858

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