Hydrochloric Acid → 1-(4-Ethylphenyl)-4-(4-ethylcyclohexyl)-1-butyn-3-ol

HRID 1491516

Reaktionsgleichung

Reaktionsgleichung von HRID 1491516
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]#[CH:10])=[CH:5][CH:4]=1)[CH3:2].[CH2:11]([CH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH:20]=[O:21])[CH2:15][CH2:14]1)[CH3:12].Cl>C1COCC1>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[C:2][CH:20]([OH:21])[CH2:19][CH:16]2[CH2:17][CH2:18][CH:13]([CH2:11][CH3:12])[CH2:14][CH2:15]2)=[CH:4][CH:5]=1)[CH3:10]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 1424251-Ethyl-4-ethynylbenzeneHCID 189527992-(4-Ethylcyclohexyl)acetaldehyde

Produkt 1

HCID 189528201-(4-Ethylphenyl)-4-(4-ethylcyclohexyl)-1-butyn-3-olAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

4-Ethylphenylacetylene (1.3 g) was dissolved in THF (20 ml), followed by dropwise adding an n-butyllithium-hexane solution (1.61M, 0.62 ml) under ice cooling with stirring, further stirring the reaction solution under ice cooling for 30 minutes, dropwise adding a solution of 2-(4-ethylcyclohexyl)acetaldehyde (1.5 g) in THF (10 ml) , raising the temperature of the reaction solution up to room temperature after completion of the addition, stirring it for 5 hours, adding dilute hydrochloric acid (5 ml) to the resulting raw solution, extracting with ethyl acetate (50 ml), washing the organic layer with water, drying over anhydrous MgSO4 and concentrating under reduced pressure, to obtain a brown oil, which was then recrystallized from an ethyl acetate-heptane mixed solution, to obtain white crystals of 1-(4-ethylphenyl)-4-(4-ethylcyclohexyl)-1-butyn-3-ol (2.3 g).

Aufarbeitung

  1. additionby dropwise adding an n-butyllithium-hexane solution (1.61M, 0.62 ml) under ice cooling
  2. stirringfurther stirring the reaction solution under ice cooling for 30 minutes
  3. additionafter completion of the addition
  4. stirringstirring it for 5 hours
  5. extractionextracting with ethyl acetate (50 ml)
  6. washwashing the organic layer with water
  7. dry with materialdrying over anhydrous MgSO4
  8. concentrationconcentrating under reduced pressure
  9. customto obtain a brown oil, which
  10. customwas then recrystallized from an ethyl acetate-heptane mixed solution

Quellen und Nachweise

ORD-Eintrag
ord-71d355a32cda4a4aab7d7e37b752ce94
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05370819

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