Acetone → 1,5-Bis[4-(trifluoromethyl)phenyl]penta-1,4-dien-3-one

Participants

Reaction Conditions

Reaction Steps

A solution of 4-trifluoromethylbenzaldehyde (64.2 g; 0.369 mol) in heptane (70 ml) is stirred under a nitrogen atmosphere, then sodium hydroxide (15 g; 10% aq), water (30 g), and bis(2-hydroxyethyl)tallowamine N-oxide (6 g) are added. Next a solution of acetone (10.7 g; 0.184 mol) in heptane (30 ml) is added at 25° C. to 35° C. over a period of two hours. The resulting slurry is then stirred for two hours at 25° C. to 30° C. Concentrated hydrochloric acid (9.4 ml) and isopropyl alcohol (48 ml) are then added and the mixture heated at reflux for 1.5 hours, and is then cooled to 20° C. The solid is filtered, washed with heptane (40 ml) and water, and is dried to afford 54.5 g of 99.9% pure title product (yield: 79.1%), mp 153° C. to 155° C.

Provenance & Evidence