Sodium Dithionite → Anthracene-1,4-diol

Reaktionsgleichung

S(S([O-])=O)([O-])=O.[Na+].[Na+].O.O1CCOCC1.[C:16]1(=[O:31])[C:29]2[C:20](=[CH:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19](=[O:30])[CH:18]=[CH:17]1>O>[OH:30][C:19]1[C:20]2[C:29](=[CH:28][C:27]3[C:22]([CH:21]=2)=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:16]([OH:31])=[CH:17][CH:18]=1

Komponenten

Versuchsvorschrift

A solution of sodium hydrosulfite (16.70 g, 42.0 mmol, 1 molar equivalent) in a water/dioxane (3/2) (250 mL) mixture is added under nitrogen to the 1,4-anthracenedione 1a (5.00 g, 24.0 mmol, 1 molar equivalent). The resulting mixture is stirred at room temperature for 3 h. Water is added and the resulting precipitate is filtered, washed with water and dried under vacuum to give the title compound as a yellow powder (3.10 g, 61%). 1H NMR (300.13 MHz, THF-d8) (ppm) 6.53 (s, 2H) 7.34-7.40 (m, 2H) 7.96-7.99 (m, 2H) 8.65 (s, 2H) 8.70 (s, 2H).