Acetyl chloride → Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-

HRID 129257

Reaktionsgleichung

Reaktionsgleichung von HRID 129257
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1([CH3:19])[C:15]2[C:10](=[CH:11][C:12]([CH3:16])=[CH:13][CH:14]=2)[C:9]([CH3:18])([CH3:17])[CH2:8][CH2:7]1.[C:20](Cl)(=[O:22])[CH3:21]>ClCCCl>[C:20]([C:13]1[C:12]([CH3:16])=[CH:11][C:10]2[C:9]([CH3:18])([CH3:17])[CH2:8][CH2:7][C:6]([CH3:19])([CH3:5])[C:15]=2[CH:14]=1)(=[O:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 811871,2,3,4-Tetrahydro-1,1,4,4,6-pentamethylnaphthaleneHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 87186Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-Ausbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of aluminum chloride (0.96 g, 7.17 mmol) in 1 mL of 1,2-dichloroethane under argon at room temperature was added a solution of 1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalene 29 (1.2 g, 5.93 mmol) and acetyl chloride (0.51 g, 6.52 mmol) in 9 mL of 1,2-dichloroethane. The reaction mixture was stirred for 1 h and then was poured onto ice water and extracted with 40% ethyl acetate/hexane. The combined organic layers were washed with saturated aqueous NaHCO3 and brine. The solution was dried over anhydrous MgSO4, filtered through a plug of silica gel, and concentrated to afford a white solid 39 (1.45 g, 99%): m.p. 54°-57° C.; Rf 0.62 (10% ethyl acetate/hexane). The structure of the product was also confirmed using IR, 1H NMR and mass spectroscopy.

Aufarbeitung

  1. additionwas poured onto ice water
  2. extractionextracted with 40% ethyl acetate/hexane
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3 and brine
  4. dry with materialThe solution was dried over anhydrous MgSO4
  5. filtrationfiltered through a plug of silica gel
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6870eb6a83cd4f5884800d5224e3fb92
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466861

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