Acetyl chloride → 1-[4-Isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-phenyl]ethanone

HRID 1677313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677313
[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])([CH3:3])[CH3:2].[C:22](Cl)(=[O:24])[CH3:23].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[CH:1]([C:4]1[C:5]([S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:13])=[O:14])=[CH:6][C:7]([C:22](=[O:24])[CH3:23])=[C:8]([O:10][CH3:11])[CH:9]=1)([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 670535032-Isopropyl-4-methoxy-1-(toluene-4-sulfonyl)-benzene

Produkt 1

HCID 670534431-[4-Isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-phenyl]ethanoneAusbeute 81,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a clear solution of 2-Isopropyl-4-methoxy-1-(toluene-4-sulfonyl)-benzene (5.3 g, 16.56 mmol) in DCE (50 ml) was added acetyl chloride (2.0 g, 24.84 mmol) and AlCl3 (3.3 g, 24.84 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 hrs and quenched by H2O (10 ml). Ten minutes after quenching, the aqueous solution was extracted into CH2Cl2. The combined extracts was washed with H2O, dried over Na2SO4, filtered and concentrated. Flashed chromatography on silica gel (0 to 30% EtOAc in Hex) gave 1-[4-Isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-phenyl]-ethanone (4.7 g, 79%) as white solid.

Aufarbeitung

  1. customquenched by H2O (10 ml)
  2. customTen minutes after quenching
  3. extractionthe aqueous solution was extracted into CH2Cl2
  4. washThe combined extracts was washed with H2O
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4346226633c541beb0a0cabd41ab6aef
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008313B2

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