Cyclopropyl methyl ketone → 1-Cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)-1,3-propanedione

HRID 1019345

Reaktionsgleichung

Reaktionsgleichung von HRID 1019345
C[O-].[Na+].[CH3:4][S:5][C:6]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:7]=1[C:8]([O:10]C)=O.[CH3:20][C:21]([CH:23]1[CH2:25][CH2:24]1)=[O:22]>C1(C)C=CC=CC=1>[CH:23]1([C:21](=[O:22])[CH2:20][C:8]([C:7]2[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][C:6]=2[S:5][CH3:4])=[O:10])[CH2:25][CH2:24]1

Komponenten

5

Edukt 3

HCID 13004Cyclopropyl methyl ketoneHCID 10942334Sodium MethoxideHCID 10944828Methyl 2-(methylthio)-4-(trifluoromethyl)benzoate

Produkt 1

HCID 111201781-Cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)-1,3-propanedioneAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
56 °C

Versuchsvorschrift

Sodium methoxide (3.51 g. 0.065M) was added to a mixture of methyl 2-methylthio-4-trifluoromethylbenzoate (12.5 g 0.050M) and cyclopropyl methyl ketone (7 ml, 0.070M) in toluene. The mixture was heated at 55-57° C. for 1 hour. Methanol was distilled under reduced pressure. After cooling to 20° C. the mixture was acidified and the organic phase washed (sodium bicarbonate solution and with water) and evaporated to give 1-cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)propane-1,3-dione as yellow crystals (14.03 g), m.p. 64° C. A yield of 92.9% was obtained. The purity of the product was 95%.

Aufarbeitung

  1. distillationMethanol was distilled under reduced pressure
  2. temperatureAfter cooling to 20° C. the mixture
  3. washthe organic phase washed (sodium bicarbonate solution and with water)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6a83322701324a0384b901be95b17a33
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06486356B2

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