Formic Acid → 4-(3-Fluorophenyl)cyclohexanone

HRID 1095245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095245
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(O)=O.O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 962WaterHCID 187879268-(3-Fluorophenyl)-1,4-dioxaspiro[4.5]decane

Produkt 1

HCID 189531424-(3-Fluorophenyl)cyclohexanoneAusbeute 93,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

The compound (18) (61.9 g), formic acid (120 g) and toluene (120 ml) were put in a reaction vessel under a nitrogen atmosphere, heated under reflux for 3 hours, and cooled slowly to room temperature. Water (300 ml) and toluene (300 ml) were added and mixed thereto. The mixture was allowed to stand until it had separated into two phases, the organic and aqueous phases, and an extractive operation to an organic phase was carried out. The organic phase was fractionated, and washed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. Then the solvent of the solution was distilled off under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=9:1 by volume) as an eluent and silica gel as a stationary phase powder and dried, giving 47.2 g of 4-(3-fluorophenyl)cyclohexanone (19). The yield based on the compound (18) was 93.7%.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. additionmixed
  4. customhad separated into two phases
  5. washwashed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThen the solvent of the solution was distilled off under reduced pressure
  8. customthe residue was purified with a fractional operation by means of column chromatography
  9. customsilica gel as a stationary phase powder and dried

Quellen und Nachweise

ORD-Eintrag
ord-da569634b3db4c19b8ee2a50a8f5eb61
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08137583B2

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