Dichloromethane → 5-Methoxy-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

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The starting material 1,1,4,4,7-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene was prepared as follows. First, a 500 flask was charged with 230 ml dichloromethane, 19 g TiCl4, and 18.3 g 2,5-dichloro-2,5-dimethylhexane, at 22° C. Next, 3-methyl anisole (12.2 g in 20 ml dichloromethane) was added dropwise over a period of an hour. After the addition was completed, the solution was heated to 35° C. and the temperature maintained for an additional 2.5 hours. The solution was then cooled to 5° C. and quenched with water. After transfer to a separatory funnel, the solution was washed with water, then twice with brine, dried over anhydrous sodium sulfate, and rotary evaporated to give a crude product (23.78 g) containing 79.4% (by area % GC) of 1,1,4,4,7-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene.

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