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

HRID 1359145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359145
[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

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The compound from Step C was mixed with 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. AlCl3 (2.3 g, 17.3 mmol) was added and the reaction stirred at room temperature overnight. 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, d, ArH), 8.02 (1H, d, ArH), 8.11 (1H, d, ArH), 8.41 (1H, d, ArH), 8.91 (1H, s, ArH).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f313c1aa751d4e14a2f724ef770a17fb
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599921B2

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