Reaction equation
[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]Participants
Procedure
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.
Workup
- additionwas poured onto ice water
- extractionextracted with 40% ethyl acetate/hexane
- washThe combined organic layers were washed with saturated aqueous NaHCO3 and brine
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered through a plug of silica gel
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3fa1428286bf4b618486380d5532a133
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05837725
Linked notes
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