Benzene → 1,4-Dibenzoylbenzene

반응식

[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:1]([C:2]1[CH:10]=[CH:9][C:5]([C:6](=[O:7])[C:2]2[CH:10]=[CH:9][CH:5]=[CH:4][CH:3]=2)=[CH:4][CH:3]=1)(=[O:11])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

반응물 4

HCID 241Benzene

HCID 313Hydrochloric Acid

HCID 7488Terephthaloyl chloride

HCID 6451240Aluminum(III) Chloride

생성물 1

HCID 763951,4-Dibenzoylbenzene

실험 절차

1,4-Dibenzoylbenzene is prepared essentially as described by Noelting and Kohn, Ber. 19, 147 (1886). Terephthaloyl dichloride (20.3 g, 0.1 mole) is dissolved in benzene (350 ml) and anhydrous aluminum chloride (30 g, 0.22 mole) is added. The mixture is heated at 70° for 7 hours, cooled to 20° and maintained at this temperature for eighteen hours with continual stirring. The reaction mixture is then added to 1 l crushed ice and 20 ml 37% hydrochloric acid. The benzene solution is washed three times with water and twice with sodium bicarbonate solution. The excess benzene is removed by distillation. The resulting crystalline material is recrystallized from dimethylformamide, yield 22 g (76% of theory) white crystals mp 158°-159°.