Reaction #2045007

ord-9aba51634b83439c8b305fedd0029c86

Reaction equation

COC(=O)C(C)Oc1ccc(NC(C)=O)cc1
2-(4-Acetylaminophenoxy)propionic acid methyl ester
COC(=O)C(C)Oc1ccc(NC(C)=O)cc1
2-(4-Acetylamino-phenoxy)-propionic acid methyl ester
CC(Oc1ccc(N)cc1)C(=O)O
17
Yield 98.1%
CC(Oc1ccc(N)cc1)C(=O)O
2-(4-Amino-phenoxy)-propionic acid
Yield 98.1%

Conditions

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

Workup

  1. 1
    Temperaturewas refluxed for 48 hours
  2. 2
    workup.DISTILLATIONExcess concentrated hydrochloric acid was distilled off in vacuum
  3. 3
    Filtrationfiltered hot
  4. 4
    Filtrationfiltered
  5. 5
    Otherdried

Procedure

A mixture of 2-(4-Acetylaminophenoxy)propionic acid methyl ester 16 (320 grams, 1.35 mol) in concentrated hydrochloric acid (8 liters) was refluxed for 48 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 17 (240 g, 81.7%) as a brown powder. The melting point was found to be 175-180° C.

Source

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