Br[C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>O.CCOCC>[O:15]([C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1A mixture containing 50.28 g of 6-bromo-2-picoline, 83.01 g of phenol and 120.86 g of potassium carbonate under an atmosphere of nitrogen was heated in an oil bath maintained at 210° C. for 20 hrs. After cooling to room temperature, the reaction mixture was dissolved in 1000 ml of H2O and 500 ml of ether. The layers were then separated and the aqueous layer extracted with ether. The combined etheral extracts were washed three times with 5% NaOH and then once with H2O. After drying the etheral layer over anhydrous Na2SO4, removal of the solvents afforded 67.3 g of an orange oil. Distillation afforded 44.32 g of colorless oil, b.p. 80°-85° at 5 mm.
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