Sodium Hydroxide → 2-(4-acetylphenoxy)propanoic Acid

HRID 1639412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639412
[C:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]([CH3:14])[C:10]([O:12]C)=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+]>O>[C:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]([CH3:14])[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 14717334Methyl 2-(4-acetylphenoxy)propanoate

Produkt 1

HCID 51606492-(4-acetylphenoxy)propanoic AcidAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of the potassium salt of 4-hydroxyacetophenone (8.8 g, 0.05 mol) in dimethylformamide (25 mL) is added methyl 2-bromopropanoate (10.2 g, 0.06 mol) over 30 minutes and stirred at 80°-90° C. for 4 hours under nitrogen. The reaction is cooled to room temperature and methylene chloride (75 mL) and water (75 mL) are added. The organic phase is separated, washed with water (100 mL), dried and concentrated to give methyl 2-(4-acetylphenoxy)propanoate (8.5 g) (yield 76%). Methyl 2-(4-acetylphenoxy)propanoate (7.0 g, 31.5 mmol) is combined with 2N NaOH (20 mL) and refluxed overnight. Water (30 mL) is added to the reaction which is then washed with methylene chloride (50 mL). It is then acidified to pH=1 with concentrated hydrochloric acid and extracted with ethyl acetate (3×100 mL). The organic phase is dried and concentrated to provide 2-(4-acetylphenoxy)propanoic acid (5.0 g) (yield 92%): m.p. 104.3° C., IR (KBr) 3000 (br, vs), 2940 (br,s), 1754 (vs), 1650 (vs); 1H NMR (CDCl3) delta 1.69 (d, J=6.8 Hz, 3H), 2.55 (s, 3H), 4.8 (q, J=6.8 Hz, 1H), 6.92 and 7.93 (dd, J=9.0 Hz, 4H).

Aufarbeitung

  1. temperaturerefluxed overnight
  2. washis then washed with methylene chloride (50 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. customThe organic phase is dried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1fc5b1b4f111433ab2060651f7aaec24
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04883901

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