Acetone → HCID 14397959, compound

Participants

Reaction Conditions

Reaction Steps

A mechanically stirred mixture of 550.6 g (1.88 mol) of 1,4-dichloro-5-hydroxy-9,10-anthracenedione (1), 413.4 g (2.14 mol) of anhydrous cesium carbonate, 444 g, (2.4 mol) of 2,4,6-trimethylbenzyl chloride, 7.06 l of acetone, and 2.31 l of N,N-dimethylformamide was heated at reflux for 23 hr. During this period, additional portions of 2,4,6-trimethylbenzyl chloride (2.5 hr, 31.7 g; 6.5 hr, 63.4 g; 20 hr, 31.7 g) and one portion of cesium carbonate (20 hr, 4.8 g) were added. The mixture was cooled to 10° C. The precipitate was collected by filtration, washed successively with hot water and methanol, then dried at 7-9 mm/50° C./20 hr to leave 621 g (78%) of 11, mp 216°-218° C., 97.9% pure by HPLC.

Provenance & Evidence