Hydrochloric Acid → Methyl(4-aminophenoxy)acetate

HRID 2405177Notes

Reaction equation

HRID 2405177 reaction equation
Cl.[NH2:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.Cl.[CH3:15]O>>[CH3:15][O:10][C:9](=[O:11])[CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([NH2:2])=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 668114882-(4-Aminophenoxy)acetic acid hydrochloride

Product 1

HCID 6422115Methyl(4-aminophenoxy)acetateYield 58.5%

Procedure

To a mixture (4-Amino-phenoxy)acetic acid HCl 60 (250 grams, 1.228 mol), in methanol (5 liters) was passed dry HCl gas at 10° C. for 1 hour and refluxed for 10 hours. Methanol (3.5 liters) was distilled and ice water (1 liter) was added and the pH was adjusted to 7.5 with K2CO3. Crude 61 was filtered, dried, and recrystallized from a mixture of Chloroform:Hexane (1:5) to give pure 61 (130 grams, 58.5%) as a light brown powder The melting point was found to be 65-66.8° C.

Workup

  1. customat 10° C.
  2. customfor 1 hour
  3. temperaturerefluxed for 10 hours
  4. distillationMethanol (3.5 liters) was distilled
  5. additionice water (1 liter) was added
  6. filtrationCrude 61 was filtered
  7. customdried
  8. customrecrystallized from a mixture of Chloroform:Hexane (1:5)

Sources & evidence

ORD record
ord-6c118c0189a34ef8a01d034439605bf3
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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