Ammonium Hydroxide → 6,7-Dichloroanthracene-1,4,9,10-tetrol

Participants

Reaction Conditions

Reaction Steps

Ten grams (32.35 mmol) of 6,7-dichloro- 1,4-dihydroxyanthraquinone were pulverized with enough NH4OH to make a paste. This was transferred to a 500 mL round bottom (RB) flask, using additional NH4OH to make the reaction mixture 0.13-0.16 M. While stirring, 6.72 grams (38.60 mmol) sodium hydrosulfite were added portionwise over 1.5 hours. Immediately after addition, the mixture was heated slowly to 55° C. on a steam bath, then heated at 55° C. for about 1.5 hours. After cooling to room temperature, the mixture was filtered, washed twice with water, and pulled dry on the funnel for a brief period. The product was dried overnight in a vacuum oven at 55-65° C. FDMS showed a mixture of starting material and product. This mixture was carried on to compound 2 of Table 1.

Provenance & Evidence