S(Cl)(Cl)=O.O[CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:8]=1.[Li+].[Cl-:24].O>CN(C=O)C>[CH3:14][O:13][C:11](=[O:12])[C:10]1[CH:15]=[CH:16][C:7]([CH2:6][Cl:24])=[CH:8][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1A 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.
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