Methanol → Methyl 3-(4-aminophenyl)propanoate

반응식

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

참가 물질

반응물 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 754513-(4-Aminophenyl)propionic acid

생성물 1

HCID 417374Methyl 3-(4-aminophenyl)propanoate수율 78%

실험 절차

SOCl2(1.5 mL) was added slowly to MeOH (6 mL) at 0˜5° C., and the mixture was stirred for 10 minutes. 3-(4-Amino-phenyl)-propionic acid (1 g, 6.05 mmol) was added thereto at the same temperature. After the temperature was elevated to room temperature, the mixture was stirred for 12 hours. After the termination of the reaction, the reactant was concentrated under reduced pressure, added with saturated sodium bicarbonate aqueous solution, and extracted with EtOAc. The organic layer was added with NaCl aqueous solution, extracted again, and then filtered by using celite. The filtrate was concentrated under reduced pressure. The residue was added with n-Hex, and then concentrated under reduced pressure again. n-Hex (20 mL) was added to the obtained solid, and the mixture was stirred under reflux for 1 hour, and then stirred at room temperature for 2 hours. The mixture was filtered to obtain the title compound (0.85 g, 78%).