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

HRID 1957826Notes

Reaction equation

HRID 1957826 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 17 (240 g, 1.103 mol), 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 off, ice water (1 liter) was added and the pH was adjusted to 7.5 with K2CO3. Crude 18 was extracted into chloroform, washed with 5% NaHCO3 solution, water, dried over Na2SO4 and distilled to give 18 (80 g, 37.2%) as a brown syrup. The structure was confirmed with NMR.

Workup

  1. customat 10° C.
  2. customfor 1 hour
  3. temperaturerefluxed for 48 hours
  4. distillationMethanol (2.5 liter) was distilled off
  5. additionice water (1 liter) was added
  6. extractionCrude 18 was extracted into chloroform
  7. washwashed with 5% NaHCO3 solution, water
  8. dry with materialdried over Na2SO4
  9. distillationdistilled

Sources & evidence

ORD record
ord-9c3d8f0ae0754a789bad5df7628cb529
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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