p-Toluenesulfonic acid → HCID 59608924, Verbindung

HRID 1047477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047477
[Br:1][CH2:2][CH2:3][C:4]1[C:12]([CH3:13])=[C:11]([CH3:14])[CH:10]=[C:9]2[C:5]=1[CH2:6][CH:7]([CH3:17])[CH:8]2OC.CC1C=CC(S(O)(=O)=O)=CC=1.BrCCC1C(C)=C(C)C=C2C=1C=C(C)C2>C1(C)C=CC=CC=1>[Br:1][CH2:2][CH2:3][C:4]1[C:12]([CH3:13])=[C:11]([CH3:14])[CH:10]=[C:9]2[C:5]=1[CH2:6][C:7]([CH3:17])=[CH:8]2

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 59608871HCID 59608871, VerbindungHCID 68740994HCID 68740994, Verbindung

Produkt 1

HCID 59608924HCID 59608924, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a hot (110° C.) solution of 6.28 g (21.13 mmol) of 4-(2-bromoethyl)-1-methoxy-2,5,6-trimethylindane in 75 ml of toluene 0.4 g of TsOH*H2O was added. This mixture was refluxed with Dean-Stark trap for 10 min and then passed through the layer of Silica Gel 60 (40-63 um, d 80 mm, l 50 mm). The Silica Gel layer was additionally washed by 300 ml of toluene. The combined organic extract was evaporated to dryness. The product was isolated by flash chromatography using a short column with Silica Gel 60 (40-63 um, d 80 mm, l 50 mm; eluent: hexanes). Yield 5.38 g (96%) of 4-(2-bromoethyl)-2,5,6-trimethyl-1H-indene.

Aufarbeitung

  1. temperatureThis mixture was refluxed with Dean-Stark trap for 10 min
  2. washThe Silica Gel layer was additionally washed by 300 ml of toluene
  3. extractionThe combined organic extract
  4. customwas evaporated to dryness
  5. customThe product was isolated by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-13d1ca53d0224456a1698d1951dcc6cc
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569532B2

Notizen zur Reaktion

Wird geladen…