Reaction #2045004

ord-38f5b847ce1f4af9b1d105bee75bf64b

Reaction equation

CCOC(=O)COc1ccc(NC(C)=O)cc1
(4-Acetylamino-phenoxy)-acetic acid ethyl ester
Cl
hydrochloric acid
→
Cl.Nc1ccc(OCC(=O)O)cc1
14
Yield 77.6%
Cl.Nc1ccc(OCC(=O)O)cc1
(4-Amino-phenoxy)acetic acid HCl
Yield 77.6%

Reactants

CCOC(=O)COc1ccc(NC(C)=O)cc1
(4-Acetylamino-phenoxy)-acetic acid ethyl ester
Cl
hydrochloric acid

Reagents

None

Conditions

Temperature
10°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.DISTILLATIONExcess concentrated hydrochloric acid was distilled off in vacuum
  2. 2
    Filtrationfiltered hot
  3. 3
    Filtrationfiltered
  4. 4
    Otherdried

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08409559B2uspto-grants-2013_04