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

HRID 1940132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1940132
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:9])[CH:6]([CH3:8])[CH3:7].[C:11]1([S:17][CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)(Cl)Cl>[CH3:7][CH:6]([CH3:8])[C:5]([C:14]1[CH:15]=[CH:16][C:11]([S:17][CH3:18])=[CH:12][CH:13]=1)=[O:9]

Komponenten

5

Edukt 3

HCID 7520ThioanisoleHCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 8525392-Methyl-1-[4-(methylthio)phenyl]-1-propanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a suspension of aluminum chloride (136 g, 1.02 mol) in chloroform (1.0 L) cooled to -10° C., was added dropwise isobutyrylchloride (115 mL, 1.10 mol). Then thioanisole (100 mL, 0.85 mol) was added dropwise. Upon completion of addition the reaction was allowed to proceed at r.t. for 1.5 h. The reaction was cooled to 10° C. and quenched by addition of water (750 mL). The organic layer was separated, washed with water (2×500 mL), saturated NaHCO3 solution (2×500 mL), brine (1×500 mL), and then dried over Na2SO4. After concentration in vacuo., the resulting crude product crystallized upon standing under high vacuum for 30 min to give the title compound as a brown solid.

Aufarbeitung

  1. additionUpon completion of addition the reaction
  2. temperatureThe reaction was cooled to 10° C.
  3. customquenched by addition of water (750 mL)
  4. customThe organic layer was separated
  5. washwashed with water (2×500 mL), saturated NaHCO3 solution (2×500 mL), brine (1×500 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationAfter concentration in vacuo
  8. custom, the resulting crude product crystallized
  9. waitupon standing under high vacuum for 30 min

Quellen und Nachweise

ORD-Eintrag
ord-4754f671d0aa4e618a4d1a07c955b1eb
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05698584

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