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

HRID 1882312Notes

Reaction equation

HRID 1882312 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.Cl.[CH3:15]O>>[CH3:15][O:9][C:8](=[O:10])[CH:7]([O:6][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:13][CH:12]=1)[CH3:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 141969882-(4-Aminophenoxy)propanoic acid

Product 1

HCID 22060471Methyl 2-(4-aminophenoxy)propanoateYield 37.2%

Procedure

To a mixture of 2-(4-Amino-phenoxy)-propionic acid 63 (240 grams, 1.103 mmol), in Methanol (4.8 liters) was passed dry HCl gas at 10° C. for 1 hour and refluxed for 48 hours. Methanol (2.5 liter) was distilled, ice water (1 liter) was added and the pH was adjusted to 7.5 with K2CO3. Crude 64 was extracted into chloroform, washed with 5% NaHCO3 solution, water, dried over Na2SO4 and distilled to give 64 (80 grams, 37.2%) as a brown syrup. The structure was confirmed with NMR. IHNMR (CDCl3) δ 1.56 (d, 3H, CH3), 2.9 (bs, 2H, —NH2), 3.72 (s, 3H, ester), 4.58 (q, 1H, CH), 6.53 (d, 2H, Ar), 6.68 (d, 2H, Ar).

Workup

  1. customat 10° C.
  2. customfor 1 hour
  3. temperaturerefluxed for 48 hours
  4. distillationMethanol (2.5 liter) was distilled
  5. additionice water (1 liter) was added
  6. extractionCrude 64 was extracted into chloroform
  7. washwashed with 5% NaHCO3 solution, water
  8. dry with materialdried over Na2SO4
  9. distillationdistilled

Sources & evidence

ORD record
ord-957a16813ec944b38b72c2cc3e763633
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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