[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Cl>CN(C=O)C.O>[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1To a solution of 5×10-2 mole of 4-hydroxy benzonitrile (VIl) in 100 ml of DMF are added little by little 5×10-2 mole of NaH so as to obtain a temperature of 25° C. Then the solution is heated to 50° C. until the release of hydrogen ceases. After cooling to 0 ° C., 5×10-2 of 3-chloro benzyl chloride (VIII) is added little by little. The reaction mixture is heated to 40 ° C. for one hour then poured into 300 ml of iced water. The resultant solid is separated by filtration then recrystallized in an ethanol-water mixture, which leads to the expected compound.
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