Triphenylphosphine → 1-(4-propylphenyl)-4-(4-(4-pentylcyclohexyl)cyclohexyl)-2Z-butene

HRID 1609432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1609432
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([C:23]1[CH:31]=[CH:30][C:26]([CH2:27][CH2:28]Br)=[CH:25][CH:24]=1)[CH2:21][CH3:22].C(C1C=CC(CCO)=CC=1)CC.CC(C)([O-])C.[K+].[CH2:50]([CH:55]1[CH2:60][CH2:59][CH:58]([CH:61]2[CH2:66][CH2:65][CH:64]([CH2:67][CH:68]=O)[CH2:63][CH2:62]2)[CH2:57][CH2:56]1)[CH2:51][CH2:52][CH2:53][CH3:54]>C1COCC1.CCOCC.C1(C)C(C)=CC=CC=1>[CH2:20]([C:23]1[CH:31]=[CH:30][C:26](/[CH:27]=[CH:28]\[CH2:68][CH2:67][CH:64]2[CH2:65][CH2:66][CH:61]([CH:58]3[CH2:57][CH2:56][CH:55]([CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:60][CH2:59]3)[CH2:62][CH2:63]2)=[CH:25][CH:24]=1)[CH2:21][CH3:22]

Komponenten

9

Edukt 5

HCID 11776TriphenylphosphineHCID 27604762-(4-Propylphenyl)ethanolHCID 111404394-(4-Pentylcyclohexyl)cyclohexylacetoaldehydeHCID 200811661-(2-Bromoethyl)-4-propylbenzeneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 867485931-(4-propylphenyl)-4-(4-(4-pentylcyclohexyl)cyclohexyl)-2Z-buteneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 7237O-XyleneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Into a flask, were placed triphenylphosphine (2.3 g, 8.8 mmol) and 4-propylphenethylbromide (2.0 g, 8.8 mmol) prepared from 4-propylphenethyl alcohol, followed by adding and dissolving xylene (10 ml), heating under reflux for 10 hours, filtering off white crystals of 4-propylphenethyltriphenylphosphoniumbromide deposited after the completion of reaction, drying the obtained white crystals (4.3 g, 8.8 mmol), dissolving the white crystals in THF (10 ml), stirring under ice cooling, adding potassium-t-butoxide (984 mg, 8.8 mmol) to the reaction solution slowly, stirring the solution at room temperature for 2 hours after the completion of dropping, adding a THF solution of 4-(4-pentylcyclohexyl)cyclohexylacetoaldehyde (2.45 g, 8.8 mmol), further stirring for 5 hours, adding ether after completion of reaction, filtering off white solid deposited, concentrating the filtrate under reduced pressure, and purifying the obtained brown oil by means of silica gel column chromatography, to obtain a mixture (1.8 g, 4.4 mmol) of 1-(4-propylphenyl)-4-(4-(4-pentylcyclohexyl)cyclohexyl)-2Z-butene and its E-isomer.

Aufarbeitung

  1. customInto a flask, were placed
  2. additionby adding
  3. temperatureheating
  4. temperatureunder reflux for 10 hours
  5. filtrationfiltering off white crystals of 4-propylphenethyltriphenylphosphoniumbromide
  6. customafter the completion of reaction
  7. stirringstirring the solution at room temperature for 2 hours after the completion
  8. stirringfurther stirring for 5 hours
  9. customafter completion of reaction
  10. filtrationfiltering off white solid
  11. concentrationconcentrating the filtrate under reduced pressure
  12. custompurifying the obtained brown oil by means of silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-31648d9c3f6b4a66a6cece36bad7101d
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05401434

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