Water → 4-Chloromethyl-2-phenylbenzoic acid methyl ester

Participants

Reaction Steps

A solution of thionyl chloride (10.0 g, 84.0 mmol) in DMF (10 mL) was added dropwise to a solution of 4-hydroxymethyl-2-phenylbenzoic acid, methyl ester (12.1 g, 50 mmol), prepared as in Example 158C, and LiCl (2.33 g, 55.0 mmol) in DMF (40 mL). After 1 hour, the reaction mixture was poured into H2O and the resulting mixture was extracted with ether (3×). The combined organic extracts were rinsed with H2O (2×), saturated aqueous NaHCO3 (3×) and brine, dried (MgSO4) and concentrated under reduced pressure to provide the desired compound (10.8 g, 83%) as a clear, colorless oil.

Provenance & Evidence