Cl[C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1[Cl:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:27][CH2:26][CH:25](C(O)=O)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>C(#N)C.O.[N+]([O-])([O-])=O.[Ag+]>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]2[CH2:27][CH2:26][C@H:25]([C:2]3[C:3](=[O:14])[C:4]4[C:9]([C:10](=[O:13])[C:11]=3[Cl:12])=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1A mixture of 2,3-dichloro-1,4-naphthoquinone (57.0 gm), 4-(4-chlorophenyl)-cyclohexane-1-carboxylic acid (60.0 gm) and silver nitrate (42.7 gm) is taken in acetonitrile (600 ml) and then a solution of ammonium persulphate (180.12 gm) in water (780 ml) is added. The mixture is heated to reflux, maintaining good stirring. The mixture was refluxed for 4 hrs. Then cooled in ice for about 1 hr after which it is filtered. The filtrate is kept aside for acetonitrile recovery. The solid is extracted with hot methylene chloride (100 ml×3). The inorganic salt is collected separately for recovery of silver. The organic layer is dried over anhydrous sodium sulphate and concentrated to get light brownish yellow solid (38.5 gm).
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