[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[CH:21]=[O:22]>CN(C=O)C.[Cu]>[O:7]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[CH:21]=[O:22])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1A solution of phenol (1.34 g, 14.3 mmol) in DMF (25 ml) was stirred with anhydrous potassium carbonate (0.99 g, 7.2 mmol) at 70°-80° C. for 40 minutes. 4-Chloro-3-pyridinecarboxaldehyde (2.02 g, 14.3 mmol) and copper bronze powder (0.10 g) were added and the resulting suspension stirred at 100°-110° C. for 2 hours. The reaction mixture was cooled, filtered and the residues washed with ether. The combined ether washings were diluted to 400 ml with more ether, washed with saturated brine (4×) and the solvent removed to give 4-phenoxy-3-pyridinecarboxaldehyde as a pale yellow crystalline solid (2.62 g); melting point 74°-75° C.; infrared max (nujol) 1590, 1695, 2760 cm-1 ; 1H NMR delta (CDCl3) 6.75 (1H broad), 7.15 (2H,d), 7.35 (1H,t), 7.50 (2H,t), 8.5-9.7 (2H,broad), 10.7 (1H,s).
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