Hydrochloric Acid → Methyl(4-aminophenoxy)acetate

HRID 1882310Notes

Reaction equation

HRID 1882310 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-a035ee5898114d57826ef170fccf823c
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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