Hydrochloric Acid → Methyl(4-aminophenoxy)acetate

HRID 638707

Reaction equation

HRID 638707 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-23114a76f8bc498c981544969feddb83
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Linked notes

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