Acetic Acid → Methyl 2-(4-aminophenoxy)propanoate

HRID 1078006Notes

Reaction equation

HRID 1078006 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)([O-])=O.C(O)(=O)C>C(OCC)(=O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 4501947Methyl 2-(4-nitrophenoxy)propanoate

Product 1

HCID 22060471Methyl 2-(4-aminophenoxy)propanoate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A solution of methyl 2-(4-nitrophenoxy)propionate (10 g, 0.044 mol) in ethyl acetate is added dropwise to a mixture of iron dust (7.37 g, 0.132 mol) in a 5% acetic acid solution at 65° C. The reaction mixture is stirred at 65° C. for 30 minutes, cooled to room temperature and filtered through diatomaceous earth. The resultant filtrate is diluted with water and extracted with ethyl acetate. The organic extracts are combined, washed sequentially with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title product as an oil which is identified by NMR spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through diatomaceous earth
  3. additionThe resultant filtrate is diluted with water
  4. extractionextracted with ethyl acetate
  5. washwashed sequentially with saturated sodium hydrogen carbonate solution and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ab7d18f8e734ed4af295b1d1704e209
Source dataset
uspto-grants-1996_08
Patent number
US05545742

Reaction notes

Loading…