Hydrochloric Acid → (4-Bromophenyl)(4-methylphenyl)methanol

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Reaction Steps

Magnesium turnings (0.39 g, 0.016 mol) were dried in a flask and then cooled under nitrogen. Anhydrous diethyl ether (3 mL) was added, followed by 4-bromotoluene (3.0 g, 1.8 mmol). The mixture was refluxed, and more anhydrous diethyl ether was added to keep the solution volume constant. The resultant Grignard solution was added dropwise to a solution of 4-bromobenzaldehyde (1.66 g, 9.0 mmol) in anhydrous diethyl ether(6 mL). The reaction was heated with reflux for 30 minutes, following which it was cooled. The cooled solution was poured into a solution of hydrochloric acid (HCl) (3.7 milliliters (mL) concentrated HCl in 17 grams of ice-water) and stirred for 1 hour (h). The resulting mixture was extracted with diethyl ether (3 times, 50 mL each), and the combined organic extracts were dried using magnesium sulfate (MgSO4) and concentrated in vacuo. Purification by flash chromatography on silica gel (petroleum ether/ethyl acetate, 90/10, v/v) afforded 1.53 grams of (4′-bromophenyl)-4-methylphenyl methanol, a yield of about 62% as a white solid. The melting point (mp) was 80-81° C.

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