2-[4-(diethylamino)phenyl]ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a three-aperture flask, 5.43 g (28.1 mmol) of p-diethylaminophenethyl alcohol, 6.26 g (61.8 mmol) of triethylamine, and 30 mL of dehydrated tetrahydrofuran were poured, and the mixture was stirred under an argon atmosphere and an ice-cooling condition. Then, 5.09 g (56.2 mmol) of chloride acrylate was delivered by drops into the reaction solution for 30 minutes. Upon completion of the dripping, the reaction solution was further stirred for 5 hours. The reaction solution was poured to 100 mL of water and then an extract was obtained therefrom by using toluene, followed by washing with water three times. The toluene solution was dried with anhydrous magnesium sulfate, and then the solvent was distilled away to purify the toluene solution by silica gel chromatography using a mixture solvent of hexane/ethyl acetate (9/1) as an eluent to thereby synthesize 3.17 g (yield: 46% by mass) of p-diethylaminophenethyl acrylate of the exemplified compound No. 21 represented by the following structural formula. Upon completion of the dripping, the reaction solution was further stirred for 5 hours an extract was obtained by washing with water three times The toluene solution was dried with anhydrous magnesium sulfate the solvent was distilled away to purify the toluene solution by silica gel chromatography to thereby synthesize 3.17 g (yield: 46% by mass) of p-diethylaminophenethyl acrylate of the exemplified compound No

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a four-aperture flask, 9.6 g (70 mmol) of p-aminophenethyl alcohol, 38.7 g (280 mmol) of potassium carbonate, and 100 mL of monochlorobenzene were poured, and the mixture was heated at 120° C. under an argon atmosphere with stirring. Then, 32.8 g (210 mmol) of ethyl iodide was delivered by drops into the mixture for 5 hours. Upon completion of the dripping, the mixture was further heated with stirring for 5 hours. The reaction solution was cooled to the room temperature and then diluted with dichloromethane, followed by washing with water three times. The dichloromethane solution was dried with anhydrous magnesium sulfate, the solvent was distilled away to purify the dichloromethane solution by silica gel chromatography using a mixture solvent of toluene/ethyl acetate (2/1) as an eluent to thereby synthesize 12.1 g (yield: 89% by mass) of p-diethylaminophenethyl alcohol. Upon completion of the dripping, the mixture was further heated with stirring for 5 hours The reaction solution was cooled to the room temperature by washing with water three times The dichloromethane solution was dried with anhydrous magnesium sulfate the solvent was distilled away to purify the dichloromethane solution by silica gel chromatography to thereby synthesize 12.1 g (yield: 89% by mass) of p-diethylaminophenethyl alcohol