Sodium Dithionite → Anthracene-1,4-diol

Participants

Reaction Steps

To a 250 ml-round-bottom flask, was added 2 g (MW 208; 0.0096 mol) of 1,4-anthracenedione (4). To it a solution of 6.6816 g (MW 174; 0.0384 mol) of sodium hydrosulfite in 50 mL of distilled water and 50 mL of 1,4-dioxane were added. The resulting mixture was stirred at room temperature for 2-3 hours. The reaction progress is checked with TLC (using CH2Cl2:hexanes:ether 1:1:0.2 as the eluant). The mixture was transferred to a 500-mL beaker slowly, cooled over an ice-water bath, and added 100 mL of distilled water. Dark green solids precipitated. The beaker was covered with aluminum foil, and placed in the refrigerator for 1 h. The solid was filtered through a glass fritted funnel and the product was washed with 30 mL of distilled water twice. The solid product was dried under vacuum to give 1.754 g (87% yield), mp 167-169° C.; 1H NMR (CDCl3 contains a small amount of p-dioxane) d 8.7 (m, 2H, C 9,10 Hs), 8.05 (m, 2H, C 5,8 Hs), 7.5 (s, 2H, C 6,7 Hs), 6.6 (s, 2H, C 2,3 Hs). The diol is insoluble in chloroform but soluble in DMSO and DMF.

Provenance & Evidence