Methanol → Methyl 2-(4-aminophenyl)acetate

HRID 2288869Notes

Reaction equation

HRID 2288869 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:17]O>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:17])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 145334-Aminophenylacetic acid

Product 1

HCID 2761030Methyl 2-(4-aminophenyl)acetate

Procedure

To a suspension of 4-aminophenylacetic acid (7.4 g; 59.0 mmol) in ca. 90 ml of methanol, was added ca. 6.0 ml of concentrated sulfuric acid. After refluxing the brown solution for 2.5 hrs, it was concentrated to a dark oil. The oil was diluted with water and basified with 10 wt % NaHCO3 to pH 9 and extracted with ethyl acetate. The organic layer was washed with water, brine and dried with Na2SO4. Evaporation in vacuo afforded 5.0 g of methyl 4-aminophenylacetate as a dark oil.

Workup

  1. temperatureAfter refluxing the brown solution for 2.5 hrs
  2. concentrationit was concentrated to a dark oil
  3. additionThe oil was diluted with water and basified with 10 wt % NaHCO3 to pH 9
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried with Na2SO4
  7. customEvaporation in vacuo

Sources & evidence

ORD record
ord-3d1ebbd142a94c1ea413147ffa75d346
Source dataset
uspto-grants-2000_07
Patent number
US06090839

Reaction notes

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