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

HRID 232057

Reaktionsgleichung

Reaktionsgleichung von HRID 232057
[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+]>ClCCl>[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 6344DichloromethaneLösungsmittel

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 dichloromethane, 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-f09bf5353bec4f68b156e63e3916b353
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851413

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