Reaktion #216439

Reaktionsgleichung

1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalene

acetyl chloride

aluminum chloride

→

solid 39

Ausbeute 100.1%

2-Acetyl-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene

Ausbeute 100.1%

Lösungsmittel

1,2-dichloroethane

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas poured onto ice water
2. 2
   Extraktionextracted with 40% ethyl acetate/hexane
3. 3
   WaschenThe combined organic layers were washed with saturated aqueous NaHCO3 and brine
4. 4
   TrocknenThe solution was dried over anhydrous MgSO4
5. 5
   Filtrationfiltered through a plug of silica gel
6. 6
   Einengenconcentrated

Vorschrift

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.

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