[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]#N)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.Cl.[OH2:28]>C(Cl)Cl>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[O:28])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1Diisobutyl-aluminum hydride (86 mL of a 1 M solution in methylene chloride, 86 mmol) was added under nitrogen dropwise over 1 h to a solution of 4′-methoxy-1,1′-biphenyl-4-carbonitrile (15.0 g, 71.7 mmol), prepared in the previous step, in 500 mL of methylene chloride at ice bath temperature. After the addition the ice bath was removed and the reaction was stirred at room temperature for 1 h. By TLC starting material remained. The reaction was cooled to ice bath temperature and an additional 60 mL (60 mmol) of the diisobutylaluminum hydride was added dropwise over 1 h. After the addition the reaction was stirred at room temperature for 16 h. At room temperature 2 N HCl was added slowly until the reaction was acidic. Additional water and methylene chloride were added and the mixture filtered. The organic layer was then separated and the aqueous layer extracted multiple times with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure to give 4′-methoxy-1,1′-biphenyl-4-carbaldehyde (12.5 g, 82%) as a pale yellow solid, MS (EI) m/z 212. Elemental Analysis for C14H12O2. Calc'd: C, 79.23; H, 5.70; N, 0.00. Found: C, 77.92; H, 5.87; N, 0.00
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