Aluminum(III) Chloride → 1-Chloro-7-hydroxy-4-nitro-9H-thioxanthen-9-one
Reaction equation
[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:17]C)[CH:12]=3)[S:7][C:6]=2[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([OH:17])[CH:12]=3)[S:7][C:6]=2[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 25 g of 1-chloro-7-methoxy-4-nitro-9H-thioxanthen-9-one, 32.1 g of anhydrous aluminum chloride, and 300 ml of 1,2-dichloroethane is heated under reflux for 1.5 hours. The mixture is concentrated, then treated with 640 ml of concentrated HCl. After 1 hour, the slurry is filtered, and then washed with 500 ml of water followed by 300 ml of 2-propanol, to afford the title compound as a gold solid, mp>300° C.