Veratrole → 6,7-dimethoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

Participants

Reaction Conditions

Reaction Steps

2,5-dichloro-2,5-dimethylhexane (2.2 g, 12 mmol), 1,2-dimethoxybenzene (1.38 g, 10 mmol), anhydrous 1,2-dichloroethane (10 mL) and anhydrous AlCl3 (200 mg) were combined in a 100 mL Schlenk flask under Ar. The mixture was heated at 60° C. for 6 h before quenching with ice water. The layers were then separated, and the aqueous layer extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The remaining residue was purified by flash column chromatography (hexanes/Ethyl acetate=10:1) to afford the title compound (1.1 g, 35% yield). 1H NMR (CDCl3): 1.27 (s, 12H), 1.67 (s, 4H), 3.86 (s, 6H), 6.77 (s, 2H); 13C NMR (CDCl3): 32.07, 34.22, 35.42, 56.01, 109.37, 137.23, 147.05.

Provenance & Evidence