Reaction #2006413

Reaction equation

NaHCO3

Na2CO3

4-(4-aminophenyl)-butyric acid

HCl

→

40

Yield 91.0%

Methyl-4-(4-aminophenyl)-butanoate

Yield 91.0%

Solvents

MeOH

Conditions

Workup

1. 1
   OtherThe solvent was evaporated under reduced pressure
2. 2
   Extractionthe aqueous phase was extracted several times with CH2Cl2
3. 3
   OtherThe crude material was purified by flash chromatography

Procedure

To a solution of 4-(4-aminophenyl)-butyric acid (5 g, 27.90 mmol) in MeOH (100 mL) at room temperature was added HCl conc. (37% 15 mL). The resulting mixture was stirred overnight at 50° C. then treated with a saturated aqueous solution NaHCO3 and Na2CO3 solid until pH 9. The solvent was evaporated under reduced pressure then the aqueous phase was extracted several times with CH2Cl2. The crude material was purified by flash chromatography using CH2Cl2/MeOH as solvent mixture yielding 40 (4.93 g, 91%) as orange solid.

Source