Fuming sulfuric acid → 1-Pentylanthracene-9,10-dione

Participants

Reaction Conditions

Reaction Steps

The strength of the oleum employed was 8.8%, and the concentration of amylbenzoylbenzoic acid in trichlorobenzene solution was 20%. To 447 grams of the oleum mixture there was added 406 grams of 20 % solution of amylbenzoylbenzoic acid in trichlorobenzene. The addition was made gradually over a 10 minute period while holding the temperature in the reaction mass below 20° C. The temperature was raised to 90° C and held at that level for 4 hours. Then, the reaction mixture was drowned in 2000 ml of cold water. The temperature was next adjusted to just below 70° C and the organic layer was separated by decantation. It was washed twice with 800 ml portions of water, then with 800 ml of water containing 5 grams of 30% sodium hydroxide and finally with another 800 ml of water. The washed trichlorobenzene-amylanthraquinone solution weighed 345 g. Vacuum distillation at 3 mm absolute pressure indicated 18.5% organic solids that were analyzed by vapor phase chromatography and found to be 94.2% amylanthraquinone. The yield of 100% of amylanthraquinone was 92.8% of theory.

Provenance & Evidence