Reaction #725891

ord-c084b1472b4042d7afa28f58c30d85b8

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%

Reactants

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

Reagents

None

Solvents

Cl
hydrochloric acid

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: US07691364B2uspto-grants-2010_04