Carbon Tetrachloride → 2-Trichloromethylanthraquinone

반응식

C[C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.O(Cl)Cl.[C:21]([Cl:25])(Cl)([Cl:23])[Cl:22]>>[Cl:22][C:21]([Cl:25])([Cl:23])[C:9]1[CH:8]=[CH:7][C:6]2[C:5](=[O:17])[C:4]3[C:13](=[CH:14][CH:15]=[CH:2][CH:3]=3)[C:12](=[O:16])[C:11]=2[CH:10]=1

참가 물질

반응물 3

HCID 5943Carbon Tetrachloride

HCID 67732-Methylanthraquinone

HCID 24646Chlorine monoxide

생성물 1

HCID 233376452-Trichloromethylanthraquinone수율 92.5%

실험 절차

2-Methylanthraquinone (5.89 g, 0.0265 mole) and dichlorine monoxide (5.77 g, 0.0664 mole) in carbon tetrachloride (70 ml) were heated in a Carrius tube as described in Example 6 at 75° for 20.25 hrs. The product which separated as a yellow crystalline solid was dissolved in methylene chloride and filtered to separate a solid (0.49 g) judged from its infrared spectra to be anthraquinone-2-carboxylic acid. The filtrate was dried (MgSO4) and the solvent removed on a rotary evaporator to give 2-trichloromethylanthraquinone as a yellow crystalline solid (8.49 g, purity by HPLC 94.26%; yield 92.5%). An aliquot of the product was recrystallized from carbon tetrachloride and then sublimed (0.1μ) to give pure anthraquinone-2-carboxylic acid, mp 157-158.2.