Triphenylcarbinol → 1,4-PHENYLENE-4,4'-BIS(2,6-DIPHENYL-4-PYRYLIUM TETRAFLUOROBORATE)

Participants

Reaction Steps

4,4'-(1,4-Phenylene)bis(2,6-diphenylpyrylium) bis(tetrafluoroborate) was prepared as follows: To a solution of terephthaldehyde (0.40 mol) and acetophenone (2.4 mol) in ethanol (1.2 L) was added a solution of potassium hydroxide (0.50 mol) in water (100 mL). The solution was heated at reflux for 24 hours. The product, 1,4-bis(1,5-dioxo-1,5-diphenylpentan-3-yl)benzene, was collected by filtration, washed with ethanol (1 L), and dried. Fluoboric acid (0.11 mol) was added over a 30 minute period to a solution of triphenylmethanol (0.11 mol) in acetic anhydride (500 mL). Stirring was continued for 2 hours after addition was complete, then 1,4-bis(1,5-dioxo-1,5-diphenylpentan-3-yl)benzene (0.05 mol) was added and the mixture heated at reflux for 1 hour. The reaction mixture was cooled to room temperature, filtered, and the collected bis(pyrylium) salt was washed with acetone (250 mL) and dried at 50° C. at reduced pressure overnight.

Provenance & Evidence