Hydrofluoric Acid → 2-Phenyl-10-anthrone
Reaction equation
C1C2C(=CC=CC=2)C=CC=1[C:11]1[CH:12]=[C:13]([CH:24]=[CH:25][CH:26]=1)[CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=O.F>>[C:11]1([C:11]2[CH:26]=[CH:25][C:24]3[C:17](=[O:19])[C:16]4[C:15](=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:14][C:13]=3[CH:12]=2)[CH:12]=[CH:13][CH:24]=[CH:25][CH:26]=1Participants
3
Procedure
First, 11.7 g of 2-[3-(2-naphthyl)benzyl]benzoic acid were added to 250 mL of liquid hydrogen fluoride, and then the mixture was stirred until hydrogen fluoride evaporated. The residue was dissolved in chloroform, and then the solution was sequentially washed with water, an aqueous solution of ammonium hydroxide, and water. After the chloroform solution had been dried with magnesium sulfate, the solvent was removed by distillation under reduced pressure. The residue was crystallized with methanol, and was then recrystallized with cyclohexane and acetone. Thus, 6.76 g of 2-phenyl-10-anthrone were obtained (in 61% yield).
Workup
- customevaporated
- dissolution