F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([O:20][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:18][CH:19]=1)([CH3:13])([CH3:11])[CH3:12]A mixture of 4-fluorobenzaldehyde (2.0 g, 0.0161 mol), 4-tert-butylphenol (2.42 g, 0.161 mol), and K2CO3 (9.0 g, 0.065 mol) in DMF (50 mL) was heated at 80° C. After 6 h, the reaction mixture was filtered into ice/water and the product was extracted with ethyl acetate. The organic layer was washed with water, dried (MgSO4), concentrated and chromatographed with 1:1 hexane/ethyl acetate to give 3.9 g (95%) of 4-(4-tert-butylphenoxy)benzaldehyde.
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