Ethanol → Ethyl 2-(4-acetamidophenoxy)propanoate

Reaktionsgleichung

[C:1]([NH:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].S(=O)(=O)(O)O.[CH2:22](O)[CH3:23]>>[C:1]([NH:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH:10]([CH3:14])[C:11]([O:13][CH2:22][CH3:23])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Komponenten

Edukt 3

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 167904892-(4-Acetamidophenoxy)propionic acid

Produkt 1

HCID 19745458Ethyl 2-(4-acetamidophenoxy)propanoateAusbeute 80 %

Versuchsvorschrift

To a solution of 2-(4-acetamidophenoxy)propionic acid (0.5 g, 2.2 mmol) in ethanol (10 mL) is added a drop of concentrated sulfuric acid and refluxed for 4 hours. The reaction is concentrated to dryness to give a residue. The residue is partitioned between water and ethyl acetate. The ethyl acetate layer is collected, dried (MgSO4), and concentrated to give ethyl 2-(4-acetamidophenoxy)propanoate (0.44 g) (yield 80%): 1H NMR (CDCl3) delta 1.27 (t, J=7.0 Hz, 3H), 1.60 (d, J=7.0 Hz, 3H), 4.25 (q, J=7.0 Hz, 2H), 4.76 (q, J=7.0 Hz, 1H), 6.84 and 7.46 (dd, J=9.0 Hz, 4H), and 8.02 (s, 1H).