Hydrochloric Acid → Methyl 4-(2-oxoethyl)benzoate

HRID 2261788

Reaktionsgleichung

Reaktionsgleichung von HRID 2261788
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][O:12]C)=[CH:6][CH:5]=1.Cl>C1COCC1.O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]=[O:12])=[CH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 54136641Methyl 4-(2-methoxyethenyl)benzoate

Produkt 1

HCID 13844675Methyl 4-(2-oxoethyl)benzoateAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 0° C. solution of 4-(2-Methoxy-vinyl)-benzoic acid methyl ester (930 mg, 4.84 mmol) in THF (50 mL) is added conc. HCl (7 mL) dropwise. After 2 h, the reaction is diluted with water and the pH is adjusted to 7. The aqueous layer is extracted with Et2O (2×200 mL). The combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed (0% to 30% EtOAC/Hex) to yield the title compound (613 mg, 71%). 1H NMR (400 MHz, CDCl3) δ 9.77 (t, 1H, J=2.2 Hz), 8.04 (d, 2H, J=8.4 Hz), 7.30 (d, 2H, J=8.8 Hz), 3.92 (s, 3H), 3.77 (d, 2H, J=2.2 Hz).

Aufarbeitung

  1. extractionThe aqueous layer is extracted with Et2O (2×200 mL)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed (0% to 30% EtOAC/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-095c00008d1441bba8000b0c5020c6ee
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846960B2

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