[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[CH:6][CH:5]=1.[H][H].[CH3:18]I>C1(C)C=CC=CC=1>[CH3:18][O:15][CH2:14][CH2:13][CH2:12][CH2:11][S:10][C:7]1[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=1To a mixture of 7.2 g of a 57% oil dispersion of sodium hydride and 125 ml of toluene was added a solution of 36.5 g of 4-(p-chlorophenylthio)butanol in 125 ml of toluene. The mixture was stirred and heated under reflux until the evolution of hydrogen ceased. It was then cooled and 25.6 g of methyl iodide was added with stirring. The resulting mixture was heated under reflux for 2 hours, cooled, washed with three portions of water saturated with sodium chloride, dried over anhydrous sodium sulfate and evaporated to dryness. The residue was distilled at reduced pressure to give 17.1 g of product, b.p. 92°-100° at 0.05 mm, ND25 1.5524.
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