Methanol → 5,10-Bis(2-hydroxypropyl)-5,10-dihydrophenazine

Participants

Reaction Conditions

Reaction Steps

40 g (0.22 mol) of phenazine are dissolved in 500 ml of anhydrous 1,2-diethoxyethane at 80° C. under an argon atmosphere. 14 g of sodium are added. The reaction mixture is stirred vigorously under reflux at 120° C. for 24 hours and cooled to room temperature. A solution of 39 g (0.66 mol) of 1,2-propylene oxide in 50 ml of 1,2-diethoxyethane is poured into the resultant 5,10-disodium 5,10-dihydrophenazine suspension. After the reaction mixture has been stirred at room temperature for 1 hour and at 50° C. for 2 hours, the precipitate is removed by filtration. All the anhydrous 1,2-diethoxyethane is distilled off on a rotary evaporator and used for the further synthesis. The solid residue, together with filtered-off precipitate, is mixed with 500 ml of methanol, and the mixture is stirred for 30 minutes. The solution is then evaporated on a rotary evaporator and transferred into a separating funnel, chloroform is added, and the mixture is washed a number of times with water and dried using magnesium sulphate. After the solvent has been distilled off, the product is purified by chromatography (silica gel column; cyclohexane/dioxane=1/1) and recrystallized from 150 ml of an acetone/water (2/1) mixture. The yield of the pale-green crystals is 22.5 g.

Provenance & Evidence