Methanol → 4-(3-Methoxy-3-oxopropyl)benzoic acid

HRID 1716092

Reaktionsgleichung

Reaktionsgleichung von HRID 1716092
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1)([OH:3])=[O:2].S(Cl)(Cl)=O.[CH3:19]O>>[CH3:19][O:13][C:12](=[O:14])[CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 8540543-(4-Carboxyphenyl)propionic Acid

Produkt 1

HCID 113102944-(3-Methoxy-3-oxopropyl)benzoic acidAusbeute 84 %

Versuchsvorschrift

To a suspension of 3-(4-carboxyphenyl)propionic acid (2.0 g, 10.1 mmol) in methanol (20 mL) was added thionyl chloride (38 μL, 0.50 mmol). The reaction mixture was stirred at room temperature for 16 h, and a clear solution was obtained. The solvent was removed under reduced pressure. The residue was taken up in ether (100 mL), washed with saturated aqueous NaHCO3 (2×50 mL) and water (50 mL). The combined NaHCO3 and water extract was acidified with concentrated HCl in an ice bath. The precipitated white solid was collected, washed with water and dried to yield 1.76 g (84%) of compound 166 as off-white solid. The material was used without further purification. mp 146-148° C. 1H NMR (400 MHz, CDCl3): δ 2.66 (t, J=7.7 Hz, 2H), 3.02 (t, J=7.7 Hz, 2H), 3.67 (s, 3H), 7.30 (d, J=8.3 Hz, 2H), 8.03 (d, J=8.1 Hz, 2H). LCMS (ES), m/z, 209 (M+H)+, 207 (M−H)−.

Aufarbeitung

  1. customa clear solution was obtained
  2. customThe solvent was removed under reduced pressure
  3. washwashed with saturated aqueous NaHCO3 (2×50 mL) and water (50 mL)
  4. extractionThe combined NaHCO3 and water extract
  5. customwas acidified with concentrated HCl in an ice bath
  6. customThe precipitated white solid was collected
  7. washwashed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-460c4d127a5f4d93a6bf438272f51e77
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799828B2

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