Sodium Dithionite → Anthracene-1,4-diol

Participants

Reaction Conditions

Reaction Steps

To 2.00 g (1.00 mmol) of 1,4-anthracenedione, a solution of 6.68 g (38.0 mmol) of sodium hydrosulfite in 50 mL of water and 50 mL of 1,4-dioxane was added. The resulting mixture was stirred at 25° C. for 3 h, and added 100 mL of water. The mixture was cooled over an ice-water bath, and the precipitated dark green solids were collected by filtration, washed twice with water, and dried under vacuum to give 1.75 g (87% yield) of 1,4-dihydroxyanthracene, mp 167-169° C.; 1H NMR d 8.70 (s, 2H, C 9,10 Hs), 8.05 (m, 2H, C 5,8 Hs), 7.50 (s, 2H, C 6,7 Hs), 6.60 (s, 2H, C 2,3 Hs).

Provenance & Evidence