Methanol → Methyl 2-(4-aminophenyl)acetate

HRID 655212Notes

Reaction equation

HRID 655212 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>>[CH3:17][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=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-amino-phenyl acetic acid (5 g, 33 mmol) in methanol (20 mL) was added concentrated sulfuric acid (2 mL) dropwise. The reaction mixture was stirred at reflux for 1.5 h, then concentrated in vacuo. The residue was partitioned between 1 M aqueous potassium carbonate and diethyl ether. The organic layer was washed with 1 M aqueous potassium carbonate, water, then dried over sodium sulfate and filtered. The filtrate was concentrated and dried in vacuo to give 4.65 g of the product as a dark yellow oil. 1H NMR 500 MHz (DMSO) δ 3.43 (s, 2H), 3.57 (s, 3H), 4.97 (s, 2H), 6.49 (d, 2H), 6.88 (d, 2H); MS (m/z) 166 [M+H+]+.

Workup

  1. temperatureat reflux for 1.5 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between 1 M aqueous potassium carbonate and diethyl ether
  4. washThe organic layer was washed with 1 M aqueous potassium carbonate, water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-0f099c34e1cb40688c1dbd6839543c5e
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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