3-Chloro-2-chloromethyl-1-propene → HCID 11096855, compound

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Reaction Steps

A solution of 2-(chloromethyl)-3-chloropropene (3.13 g, 25 mmol) and sodium p-toluenesulfmate (4.60 g, 25 mmol) in methanol (50 mL) was heated under reflux for 24 hours. The solvent was evaporated on a rotary evaporator and the residue was extracted between dichloromethane and water. The organic layer was dried (anhydrous MgSO4) and evaporated to give crude product (4.7 g) which, after purification by column chromatography on a silica-gel column using ethyl acetate/n-hexane 1:9 as eluent, gave pure product (2.7 g, 44% yield). 1H-NMR (CDCl3) δ (ppm): 2.46 (s, 3H, CH3Ar); 3.92 (s, 2H, CH2SO2); 4.19 (s, 2H, CH2Cl); 5.02 (s, 1H, vinylic-H); 5.45 (s, 1H, vinylic-H); 7.37 and 7.77 (2d, 4H, ArH).

Provenance & Evidence