Methanol → Methyl 3-(4-aminophenyl)propanoate

반응식

S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1.[CH3:17]O>>[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=1

참가 물질

반응물 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 754513-(4-Aminophenyl)propionic acid

생성물 1

HCID 417374Methyl 3-(4-aminophenyl)propanoate수율 99%

실험 절차

Under ice-cooling, thionyl chloride (15 mL, 206 mmol) was added dropwise to methanol (60 mL), and the mixture was stirred for 10 min. 3-(4-Aminophenyl)propanoic acid (10.1 g, 61.1 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 18 hr. The solvent and excess thionyl chloride were evaporated under reduced pressure, and water and saturated aqueous sodium hydrogencarbonate were added. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained solid was washed with hexane to give the title compound (10.9 g, yield 99%) as pale-brown prism crystals.