Thioanisole → 2-Methyl-1-[4-(methylthio)phenyl]-1-butanone

HRID 367362

Reaktionsgleichung

Reaktionsgleichung von HRID 367362
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][CH:6]([CH2:10][CH3:11])[C:7](Cl)=[O:8].[C:12]1([S:18][CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)(Cl)Cl>[CH3:5][CH:6]([CH2:10][CH3:11])[C:7]([C:15]1[CH:16]=[CH:17][C:12]([S:18][CH3:19])=[CH:13][CH:14]=1)=[O:8]

Komponenten

5

Edukt 3

HCID 7520ThioanisoleHCID 93697Butanoyl chloride, 2-methyl-HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 154806432-Methyl-1-[4-(methylthio)phenyl]-1-butanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A 500 mL RBF equipped with a mechanical stirrer was charged with AlCl3 (35.4 g) and CHCl3 (300 mL) and cooled in an ice bath. Then 2-methylbutanoyl chloride (31.4 g) was added over 0.5 h to the ice-cold suspension. Keeping the internal temperature <10° C., thioanisole (31.2 mL) was added dropwise over 1 h. After completion of addition, the resulting mixture was stirred at r.t. for 2 h. The resulting suspension was poured onto an ice-water mixture and stirred until decoloraton. The organic layer was separated, washed with water, dried over Na2SO4 and concentrated to dryness. The resulting white solid was swished in hexane and collected by filtration to give the title compound as a white solid. 1H NMR(CD3COCD3): δ0.88 (3H, t), 1.12 (3H, d), 1.47 (1H, m), 1.78 (1H, m), 2.57 (3H, s), 3.49 (1H, m), 7.37 (2H, d), 7.93 (2H, d).

Aufarbeitung

  1. customA 500 mL RBF equipped with a mechanical stirrer
  2. temperaturecooled in an ice bath
  3. additionwas added dropwise over 1 h
  4. additionAfter completion of addition
  5. stirringstirred until decoloraton
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated to dryness
  10. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-05fdd62f7a5f4cfe97773d02a314146e
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133292

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