Methanol → Methyl 3-(4-aminophenyl)propanoate

HRID 417364

Reaction equation

HRID 417364 reaction equation
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

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 754513-(4-Aminophenyl)propionic acid

Product 1

HCID 417374Methyl 3-(4-aminophenyl)propanoateYield 98%

Procedure

Thionyl chloride (Aldrich, 4.08 g, 2.5 ml, 34.3 mmol) was added dropwise to anhydrous MeOH (10mL) in ice-water-salt bath. After 20 min, 3-(4-aminophenyl)propionic acid (Trans World Chemicals, 1.7 g, 10.3 mmol) was added and the reaction mixture was allowed to stir at rt overnight. The resulting reaction mixture was concentrated in vacuo and the residue was diluted with EtOAc, washed with sat. aqueous NaHCO3, water, and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to give methyl 3-(4-aminophenyl)propanoate (1.80 g, 98%).

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additionthe residue was diluted with EtOAc
  4. washwashed with sat. aqueous NaHCO3, water, and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd6c85ae321c41b483fe3315c256cc1f
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Linked notes

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