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

HRID 2405176Notes

Reaction equation

HRID 2405176 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 59 (375 grams, 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 60 (250 grams, 77.6%) as a wheat colored powder. The melting point was found to be 224-226° C. The structure was confirmed with NMR. IHNMR (D2O) δ 4.68(s, 2H, OCH2), 3.65(s,3H,ester), 7.0(d,2H,Ar), 7.30(d,2H,Ar

Workup

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

Sources & evidence

ORD record
ord-b1d27f31da5843468f76c9750cfff825
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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