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Sulfuric Acid → 4-(4-tert-Butylphenyl)-2-(propan-2-yl)-1H-indene

HRID 2099601
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2099601
[BH4-].[Na+].[CH:3]([CH:6]1[CH2:14][C:13]2[C:8](=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=3)[CH:10]=[CH:11][CH:12]=2)[C:7]1=O)([CH3:5])[CH3:4].C1(C)C=CC=CC=1.S(=O)(=O)(O)O>CO>[CH:3]([C:6]1[CH2:14][C:13]2[C:8]([CH:7]=1)=[C:9]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:17][CH:16]=1)[CH:10]=[CH:11][CH:12]=2)([CH3:5])[CH3:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 4311764Sodium borohydrideHCID 231055462-Isopropyl-7-(4'-tert-butylphenyl)-1-indanone

Produkt 1

HCID 179804054-(4-tert-Butylphenyl)-2-(propan-2-yl)-1H-indeneAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

4.83 g of sodium borohydride and 39.1 g of 2-isopropyl-7-(4′-tert-butylphenyl)-1-indanone together with 11.8. ml of toluene are placed in a reaction vessel. At 50° C., 22.5 ml of methanol are slowly added and the reaction mixture is stirred for 6 hours at 50° C. After cooling to room temperature, 50 ml of 2N sulfuric acid are added and the mixture is stirred vigorously for another 30 minutes. The mixture is subsequently transferred to a separating funnel, the phases are separated and the aqueous phase is shaken twice with a total of 60 ml of 2N sulfuric acid. The organic phases are combined and dried over magnesium sulfate. The solvent of the reaction mixture is removed virtually completely and 200 ml of toluene and 0.4 g of p-toluenesulfonic acid are subsequently added to the residue. Water is distilled from the reaction mixture by heating for 1.5 hours on a water separator until reaction is complete. The reaction mixture is subsequently washed once with 100 ml of saturated sodium hydrogen carbonate solution and dried over magnesium sulfate. After separating off the magnesium sulfate, the residue is dried in an oil pump vacuum. This gives 35.7 g of 2-isopropyl-4-(4′-tert-butylphenyl)indene (total yield: 96%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. stirringthe mixture is stirred vigorously for another 30 minutes
  3. customThe mixture is subsequently transferred to a separating funnel
  4. customthe phases are separated
  5. stirringthe aqueous phase is shaken twice with a total of 60 ml of 2N sulfuric acid
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent of the reaction mixture is removed virtually completely
  8. addition200 ml of toluene and 0.4 g of p-toluenesulfonic acid are subsequently added to the residue
  9. distillationWater is distilled from the reaction mixture
  10. temperatureby heating for 1.5 hours on a water separator until reaction
  11. washThe reaction mixture is subsequently washed once with 100 ml of saturated sodium hydrogen carbonate solution
  12. dry with materialdried over magnesium sulfate
  13. customAfter separating off the magnesium sulfate
  14. customthe residue is dried in an oil pump vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1a12df8392fe48d380f29ff515f4c035
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07569651B2

Notizen zur Reaktion

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