Trifluoroacetic anhydride → 6-methoxy-7-methyl-3,4-dihydronaphthalen-1(2H)-one

HRID 1859811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1859811
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[CH3:9].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl.CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][C:8]=1[CH3:9])[C:13](=[O:15])[CH2:12][CH2:11][CH2:10]2

Komponenten

5

Edukt 2

HCID 9845Trifluoroacetic anhydrideHCID 186264724-(3-Methoxy-4-methylphenyl)butanoic acid

Produkt 1

HCID 113559636-methoxy-7-methyl-3,4-dihydronaphthalen-1(2H)-oneAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 5.6 g (26.9 mmol) of 4-(3-methoxy-4-methylphenyl)butanoic acid in 100 mL of CH2Cl2 was cooled in ice and treated dropwise with 25 mL of trifluoroacetic anhydride. After stirring at 0° C. for 1 hour, the solution was diluted with Et2O and washed twice with 5% NaOH, then with saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product. Chromatography on silica gel, eluting with CH2Cl2 gave 2.79 g (54.7% yield) of the product as a white solid, mp 104-107° C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 191 (M+H+).

Aufarbeitung

  1. washwashed twice with 5% NaOH
  2. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  3. waitleft the crude product
  4. washChromatography on silica gel, eluting with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-845fbe76686048abbce0de3cb43ba391
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06528535B2

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