Dichloromethane → 4,4'-Dichlorobenzhydryl chloride

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Thionyl chloride (10 mL, 137 mmol) was added dropwise to 4-chlorobenzhydrol (12.66 g, 50 mmol) in CH2Cl2 (200 mL) under nitrogen over 15 min. After 18 h and solvent removal in vacuo, the crude product was dissolved in methylene chloride (250 mL) and washed with saturated NaHCO3 (3×50 mL), dried over Na2SO4, and concentrated in vacuo to a thin, amber oil (12.53 g). Upon standing at room temperature for 1 h, crystallization occured to give pure product (12.5 g, 88.4%) as a white solid, mp 61°-64° C. DCI/MS (M+1) 235. 400 MHz 1H NMR (CDCl3) δ: 7.35 (m, 8H), 6.05 (s, 1H).

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