[OH-:1].[K+].O[C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CN(C)C=O.O>[CH2:13]([O:1][C:10]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:11]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]In a 100 ml four-necked flask, 2.79 g (42.3 mM) of 85 wt % potassium hydroxide was suspended in 30 ml of dimethylformamide, and 10 ml of a dimethylformamide solution containing 5.28 g (43.2 mM) of hydroxybenzaldehyde was added thereto dropwise while maintaining the system at 20° C. or lower, followed by aging at 30° C. for 1 hour. To the system was added 9.58 g (32.9 mM) of 1-bromopentadecane, followed by aging at 70° C. for 21 hours. The reaction mixture was dispersed in water and extracted with toluene. The extract was washed with water and concentrated to give 11.03 g of a slightly colored viscous liquid. Recrystallization from hexane gave 8.91 g of p-pentadecanoxybenzaldehyde (purity: 98.3%).
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