Methanol → Methyl 4-aminobenzenebutanoate

HRID 1807290Notes

Reaction equation

HRID 1807290 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:8][CH:7]=1.[CH3:18]O>>[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 270494-(4-Aminophenyl)butanoic acid

Product 1

HCID 88628Methyl 4-aminobenzenebutanoateYield 94%

Procedure

Thionyl chloride (2.5 mL, 4.08 g, 34.3 mmol) was added to stirred anhydrous methanol (10 mL) at 0° C. After 20 mins, 4-(4-AMINOPHENYL)BUTYRIC ACID (1.85 g, 10.3 mmol, Aldrich) was added and the mixture was stirred at rt for 16 hrs. The reaction mixture was concentrated and the residue dissolved in ethyl acetate, washed with sat. NaHCO3, water, and sat. NaCl, dried over Na2SO4 and concentrated to give methyl 4-(4-aminophenyl)butanoate (1.88 g, 94%) as a light brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with sat. NaHCO3, water, and sat. NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2a0ec15f23234064b17641032750b9f7
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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