Acetic Acid → 2-(4-Acetamidophenoxy)propionic acid

HRID 2254345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2254345
C([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)(=O)C.S(O)(O)(=O)=O.[NH2:21]O.C(=O)([O-])[O-].[Na+].[Na+].[C:29]([OH:32])(=O)[CH3:30]>S(=O)(=O)(O)O.O>[C:29]([NH:21][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1)(=[O:32])[CH3:30]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 159255Hydroxylamine, sulfate (1:1)HCID 51606492-(4-acetylphenoxy)propanoic Acid

Produkt 1

HCID 167904892-(4-Acetamidophenoxy)propionic acidAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 2-(4-acetylphenoxy)propionic acid (1.5 g, 7.2 mmol), hydroxylamine sulfate (0.72 g, 4.4 mmol), and concentrated sulfuric acid (2 drops) in acetic acid (30 mL) is refluxed for 4.25 hours. The reaction is quenched with sodium carbonate (0.25 g, 2.4 mmol) and concentrated to give a residue. The reaction residue is dissolved in water (50 mL) and extracted with ethyl acetate (2×100 mL). The ethyl acetate extract is dried and concentrated to give 2-(4-acetamidophenoxy)propionic acid (1.53 g) (yield 95%): m.p. 170°-172° C.; IR (KBr) 3400 (vs), 2900 (s) 1730 (vs), 1630 (vs), and 1603 (vs); 1H NMR (DMSO-d6) delta 1.47 (d, J=6.8 Hz, 3H), 1.87 (s,3H), 2.06 (s,3H), 4.65 (q, J=6.8 Hz, 1H), 6.73 and 7.42 (dd, J=9.0 Hz, 4H).

Aufarbeitung

  1. concentrationconcentrated
  2. customto give a residue
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. extractionThe ethyl acetate extract
  5. customis dried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5e20147a912140a3916ef8715e9811bd
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05235090

Notizen zur Reaktion

Wird geladen…