[CH2:1]([OH:8])C1C=CC=CC=1.N1C=CC=C[CH:10]=1.S(Cl)(Cl)=O.[ClH:19].[Cl-].[C:21]1([CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH3:1][O:8][C:22]1[CH:23]=[CH:24][C:25]([CH3:10])=[CH:26][C:21]=1[CH2:27][Cl:19]3.23 g (21.22×10-3 mol) of benzyl alcohol and 50 cm3 of anhydrous toluene are introduced into a 100-cm3 three-necked flask. Under argon, while stirring and cooling the reaction mixture, 1.70 cm3 (21.10×10-3 mol) of pyridine dried over potassium hydroxide are introduced, followed by 3.5 cm3 (47.98×10-3 mol) of thionyl chloride. A white precipitate forms and hydrogen chloride is evolved. After introduction of the reactants, reaction is allowed to proceed at room temperature for approximately 24 h. The mixture is then poured into an ice bath and stirred for 1 h. The organic phase is recovered, washed with water, saturated sodium bicarbonate solution and saturated sodium chloride solution and lastly dried over MgSO4. After evaporation to dryness, the residue is purified by vacuum distillation and 2.5 g (14.65×10-3 mol) of the expected chloride are obtained, equivalent to a 69% yield.
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