[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([OH:11])[CH3:10])=[CH:4][CH:3]=1.[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)([O-:14])=[O:13].Cl>C1C=CC=CC=1.O.[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][CH:9]([CH3:10])[O:11][CH:19]2[C:18]2[CH:21]=[CH:22][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=2)=[CH:6][CH:7]=111.94 g (70 mM) of 1-(4-chlorophenyl)-2-propanol [J. Med. Chem. 21, 454 (1978)] and 10.57 g (70 mM) of 4-nitrobenzaldehyde were dissolved in 70 ml of anhydrous benzene, then 9.56 g (70 mM) of freshly prepared anhydrous zinc chloride were added and dry hydrochloric acid gas was led into the mixture for 3 hours. Then the mixture was refluxed for 1.5 hours, cooled, diluted with water and the layers were separated. The organic layer was first washed with water then with a solution of sodium hydrogen carbonate, dried and evaporated. The resulting crude product was recrystallized from ethanol.
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