Water → 2-(4-Pyridyl)propane-1,2-diol

HRID 1719707

Reaktionsgleichung

Reaktionsgleichung von HRID 1719707
[Mn]([O-])(=O)(=O)=O.[K+].S([O-])([O-])(=O)=[O:8].[Mg+2].[C:13]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)([CH3:15])=[CH2:14].[OH2:22]>CC(C)=O.C1(C=CC(O)=CC=1)O>[N:19]1[CH:20]=[CH:21][C:16]([C:13]([OH:8])([CH3:15])[CH2:14][OH:22])=[CH:17][CH:18]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 529351Pyridine, 4-(1-methylethenyl)

Produkt 1

HCID 202664302-(4-Pyridyl)propane-1,2-diol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 785HydroquinoneKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of potassium permanganate (10.6 g) and magnesium sulphate (4.0 g) in water (250 cm3) was added at 0° to a mechanically stirred solution of 4-isopropenyl pyridine (14.8 g) in acetone (150 cm3) over 0.5 hours. After a further 0.5 hours at 0°, the mixture was warmed to room temperature over 1 hour, hydroquinone (0.01 g) was added and the mixture was filtered through "Avicel" (Trademark) to remove manganese dioxide. Solvents were removed in vacuo yielding a viscous oil which was chromatographed on silica ("Merck" 60.9385) eluting with methanol:chloroform, 1:19, to give 2-(4-pyridyl)propan-1,2-diol as an oil (6.0 g).

Aufarbeitung

  1. filtrationthe mixture was filtered through "Avicel" (Trademark)
  2. customto remove manganese dioxide
  3. customSolvents were removed in vacuo
  4. customyielding a viscous oil which
  5. customwas chromatographed on silica ("Merck" 60.9385)
  6. washeluting with methanol

Quellen und Nachweise

ORD-Eintrag
ord-a63b00e2f17147718489bb298be276ac
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04542132

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