Hydrochloric Acid → 2-(4-Aminophenoxy)acetic acid hydrochloride

HRID 638706Notes

Reaction equation

HRID 638706 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13]C(=O)C)=[CH:9][CH:8]=1)C.[ClH:18]>>[ClH:18].[NH2:13][C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]([OH:17])=[O:3])=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 309738Ethyl 2-(4-acetamidophenoxy)acetate

Product 1

HCID 668114882-(4-Aminophenoxy)acetic acid hydrochlorideYield 77.6%

Conditions

Temperature
10 °C

Procedure

A mixture (4-Acetylamino-phenoxy)-acetic acid ethyl ester 13 (375 g, 1.582 mmol), in concentrated hydrochloric acid (9.36 liters) was refluxed for 12 hours. Excess concentrated hydrochloric acid was distilled off in vacuum and filtered hot. The mixture was cooled to 10° C., filtered and dried to give pure 14 (250 g, 77.6%) as a wheat colored powder. The melting point was found to be 224-226° C. The structure was confirmed with NMR.

Workup

  1. distillationExcess concentrated hydrochloric acid was distilled off in vacuum
  2. filtrationfiltered hot
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-f28df230f2a842f6bd81173f55feb8ca
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Reaction notes

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