Dichloromethane → 3-(Trichloromethyl)pyridine

Reaction equation

Cl.[Cl:2][C:3]([Cl:11])([Cl:10])[C:4]1[CH:5]=[NH+:6][CH:7]=[CH:8][CH:9]=1.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:2][C:3]([Cl:11])([Cl:10])[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

Procedure

The 3-trichloromethylpyridinium hydrochloride salt (2836 g, 12.17 moles) was placed in a 22-liter pot with 2800 ml of methylene chloride and 2600 ml of water. A solution of 1000 g of sodium carbonate in 4300 ml of water was then added slowly so that the gassing could be controlled. The temperature was maintained with an ice bath between 15°-20° C. The lower organic phase was then separated and was dried with magnesium sulfate. The mixture was filtered and the methylene chloride was removed by rotary evaporation. The concentrated material was distilled at 77°-79° C. and 0.5 mm Hg giving 1918 g of the desired 3-trichloromethylpyridine product. The yield was 80%.