Ethanol → Ethyl 2-(4-acetamidophenoxy)propanoate

HRID 1639414Notes

Reaction equation

HRID 1639414 reaction equation
[C:1]([NH:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].S(=O)(=O)(O)O.[CH2:22](O)[CH3:23]>>[C:1]([NH:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH:10]([CH3:14])[C:11]([O:13][CH2:22][CH3:23])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 167904892-(4-Acetamidophenoxy)propionic acid

Product 1

HCID 19745458Ethyl 2-(4-acetamidophenoxy)propanoateYield 80%

Procedure

To a solution of 2-(4-acetamidophenoxy)propionic acid (0.5 g, 2.2 mmol) in ethanol (10 mL) is added a drop of concentrated sulfuric acid and refluxed for 4 hours. The reaction is concentrated to dryness to give a residue. The residue is partitioned between water and ethyl acetate. The ethyl acetate layer is collected, dried (MgSO4), and concentrated to give ethyl 2-(4-acetamidophenoxy)propanoate (0.44 g) (yield 80%): 1H NMR (CDCL3) delta 1.27 (t, J=7.0 Hz, 3H), 1.60 (d, J=7.0 Hz, 3H), 4.25 (q, J=7.0 Hz, 2H), 4.76 (q, J=7.0 Hz, 1H), 6.84 and 7.46 (dd, J=9.0 Hz, 4H), and 8.02 (s, 1H).

Workup

  1. temperaturerefluxed for 4 hours
  2. concentrationThe reaction is concentrated to dryness
  3. customto give a residue
  4. customThe residue is partitioned between water and ethyl acetate
  5. customThe ethyl acetate layer is collected
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a44f599a4e0a428c823cbc415b698656
Source dataset
uspto-grants-1989_11
Patent number
US04883901

Reaction notes

Loading…