Hydrochloric Acid → Methyl(4-aminophenoxy)acetate

HRID 1957823Notes

Reaction equation

HRID 1957823 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 of (4-Aminophenoxy)acetic acid HCl 14 (250 g, 1.228 mol), in methanol (5 L) was passed dry HCl gas at 10° C. for 1 hour and refluxed for 10 hours. Methanol (3.5 liters) was distilled off, ice water (1 liter) was added and the pH was adjusted to 7.5 with K2CO3. Crude 15 was filtered, dried and recrystallised from a mixture of chloroform:hexane (1:5) to give pure 15 (130 g, 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 off
  5. additionice water (1 liter) was added
  6. filtrationCrude 15 was filtered
  7. customdried
  8. customrecrystallised from a mixture of chloroform:hexane (1:5)

Sources & evidence

ORD record
ord-7432d99ecb824b71b9131da5cf7d3322
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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