Thionyl Chloride → 8-Acetyl-3-methoxy-benzo[c]chromen-6-one

HRID 987590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987590
[C:1]([C:4]1[CH:5]=[C:6]([C:20]([OH:22])=[O:21])[C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2OC)=[CH:8][CH:9]=1)(=[O:3])[CH3:2].O=S(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[C:1]([C:4]1[CH:9]=[CH:8][C:7]2[C:10]3[C:11](=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)[O:22][C:20](=[O:21])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 113471004-Acetyl-2',4'-dimethoxy-biphenyl-2-carboxylic acid

Produkt 1

HCID 103332378-Acetyl-3-methoxy-benzo[c]chromen-6-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

The compound from Step D was dissolved in 1,2-dichloroethane (60 mL) and SOCl2 (1.7 mL, 23 mmol) was added. The mixture was refluxed for 90 min and then cooled to 0° C. at which point AlCl3 (2.3 g, 17.3 mmol) was added. The resulting reaction mixture was stirred overnight at room temperature. The solvent was removed and the crude product chromatographed on silica gel with hexane/ethyl acetate (1:1) to yield 5.1 g (90%) of the title compound. 1H-NMR (400 MHz, CDCl3) δH 2.74 (3H, s, COCH3), 3.94 (3H, s, OCH3), 6.92 (1H, s, ArH), 6.99 (1H, ArH), 8.02 (1H, d, ArH), 8.11 (1H, d, ArH), 8.41 (1H, d, ArH), 8.91 (1H, s, ArH).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 90 min
  2. additionwas added
  3. customThe resulting reaction mixture
  4. customThe solvent was removed
  5. customthe crude product chromatographed on silica gel with hexane/ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-129d764ffde641419e1eb6826055cef4
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06632835B2

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