Sulfuric Acid → 1,3-Dimethoxy-2-(3-phenylpropyl)benzene

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A solution of 8.70 g (63 mmol) of 1,3-dimethoxybenzene in 164 mL of anhydrous tetrahydrofuran was stirred at -20° C. while 1.6M n-butyllithium in hexane (42.1 mL; 67.2 mmol) was added dropwise, over 20 min. The solution was stirred at -20° C. for 3 hr and then allowed to warm to -5° C. whereupon 15.66 g (63.6 mmol) of 1-iodo-3-phenylpropane was added over 15 min. The reaction mixture was stirred at -5° C. for 1 hr and then at room temperature for 3 d. After being recooled to -5° C., the reaction mixture was decomposed by the addition of 1.5N aqueous sulfuric acid. Water was added and the mixture was worked-up with ether in the usual manner. The residue was treated with 100 mL of hexane and the mixture was filtered. Removal of the solvent in vacuo gave 15.28 g (94.7%) of the title compound as a yellow oil.

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