Water → 2-(4-Pyridyl)propane-1,2-diol

Participants

Reaction Steps

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).

Provenance & Evidence