1-Bromooctane → Benzophenone

Participants

Reaction Conditions

Reaction Steps

2,4-dihydroxybenzophenone (5 g, 23 mmol) and polyethylenglycol (PEG 6000) (1 g) in toluene (25 ml) and NaOH 30% (6,26 g, 47 mmol) were loaded into a 100 ml three-necked flask. The solution was kept under reflux with Dien-Stark to remove water. The solution was cooled at 40° C. Dimethylsulfoxide (DMSO) (7 ml) and octylbromide (8 ml, 47 mmol) were added and the solution thus obtained was kept under reflux with Dien-Stark for 8 hours. NaOH 30% (30 ml) and methylisobutylketone (MIBK) (10 ml) were added. The aqueous phase containing the unreacted dihydroxybenzophenone sodium salt was separated from the solution. The organic phase was washed with water. The aqueous phase was reextracted with MIBK (10 ml). Both aqueous and organic phases were cloudy (the organic phase was filtered on silica). After removal of the solvent from the organic phase the crude product was dissolved in cool ethyl-acetate (9 ml) and methanol (65 ml) was added. The product crystallized at —5° C. The product was recrystallized from methanol at 30° C. cooling up to 10° C. (yield 35%; m.pt. 37,7-38,1° C.).

Provenance & Evidence