Hydrochloric Acid → 3,4-Bis(4-methoxyphenyl)hex-3-ene

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Zinc dust (654 mg, 10.0 mmol) was slurried in 20 ml dry tetrahydrofuran under an inert atmosphere, and a solution of titanium tetrachloride (0.55 ml, 5.0 mmol) in 3 ml dry benzene was added. The resulting mixture was refluxed overnight to form active Ti(II) reagent, and a solution of para-methoxypropiophenone (500 mg, 3.0 mmol) in 5 ml dry tetrahydrofuran was added. After refluxing for twelve hours, the solution was cooled to room temperature, poured into 50 ml 2 N aqueous hydrochloric acid, and extracted with ether. The ether extracts were combined, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated by solvent removal at the rotary evaporator. The residue was purified by chromatography on silica gel to give 410 mg (91%) dimestrol identified by ir, nmr, and mass spectra; mp 124°.

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