Trifluoroacetic acid → 2-(Phenylmethyl)-1-phenyloctane

HRID 1377228

Reaktionsgleichung

Reaktionsgleichung von HRID 1377228
[C:1]1([CH:7](O)[C:8]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.[H][H]>[Pd].O>[C:1]1([CH2:7][CH:8]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 539411361,3-Diphenyl-2-n-hexyl-2-propen-1-olHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 229196762-(Phenylmethyl)-1-phenyloctaneAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In a 2-liter three-necked flask equipped with a stirring device and a nitrogen substituting device, 169.6 g of 1,3-diphenyl-2-n-hexyl-2-propen-1-ol, 0.4 milliliters of trifluoroacetic acid and 17 g of a Pd-C catalyst (a 5% product, containing 55.9% of water) were introduced, and stirred at 50° C. and contacted with hydrogen gas. After stirring for 30 hours, the catalyst was filtered off, water was added, and an extraction was carried out with n-heptane. After washing with sodium hydrogencarbonate and water, the solution was dried with anhydrous sodium sulfate. After removing off the solvent by a rotary evaporator and dissolving the residue in a small amount of n-heptane, a separating operation was carried out by a column chromatography with silica gel. By removing off the solvent again and carrying out a distillation under a decreased pressure, to obtain 98.9 g of 1,3-diphenyl-2-n-hexyl propane as colorless liquid.

Aufarbeitung

  1. customIn a 2-liter three-necked flask equipped with a stirring device
  2. additionwere introduced
  3. stirringAfter stirring for 30 hours
  4. filtrationthe catalyst was filtered off
  5. additionwater was added
  6. extractionan extraction
  7. washAfter washing with sodium hydrogencarbonate and water
  8. dry with materialthe solution was dried with anhydrous sodium sulfate
  9. customAfter removing off the solvent
  10. customby a rotary evaporator
  11. dissolutiondissolving the residue in a small amount of n-heptane
  12. customBy removing off the solvent again
  13. distillationa distillation under a decreased pressure

Quellen und Nachweise

ORD-Eintrag
ord-01465d61d7f5453ab73d0eecb4f2243c
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663440

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