Reaction #2006410

Reaction equation

4-aminophenylacetic acid

HCl

methanol

→

3

Yield 74.0%

Methyl-4-aminophenylacetate

Yield 74.0%

Conditions

Workup

1. 1
   OtherThe reaction mixture was then quenched with a saturated aqueous solution of NaHCO3
2. 2
   OtherThe methanol was evaporated under reduced pressure
3. 3
   Extractionthe aqueous layer was extracted several times with AcOEt
4. 4
   DryingThe combined organic extracts were dried over (MgSO4)
5. 5
   Otherevaporated
6. 6
   OtherThe crude residue was purified by flash chromatography

Procedure

To a solution of 4-aminophenylacetic acid (10 g, 66.2 mmol) in methanol (150 mL) at room temperature was added HCl conc. (37% 25 mL). The mixture became yellow and was stirred overnight. The reaction mixture was then quenched with a saturated aqueous solution of NaHCO3. The methanol was evaporated under reduced pressure and the aqueous layer was extracted several times with AcOEt. The combined organic extracts were dried over (MgSO4) and evaporated. The crude residue was purified by flash chromatography using hexane/AcOEt (4:1) as solvent mixture yielding 3 as a yellow oil (9.44 g, 74%).

Source