Methyl Acrylate → 1,1,3-Trichloro-3-carbomethoxypropane-1-phosphonic dichloride

Participants

Reaction Steps

To 11.8 g (0.05 mole) distilled trichloromethane phosphonic dichloride and 8.6 g (0.1 mole) methylacrylate was added a solution of 134 mg (1 mmole) anhydrous cupric chloride and 206 mg (1.5 mmole) triethylammonium chloride in 5 ml acetonitrile. The homogeneous solution was heated in the absence of air in a sealed ampoule at 125° for 15 hours. After cooling, the contents of the ampoule was subjected to distillation. 12.9 g 1:1 adduct, 1,1,3-trichloro-3-carbomethoxypropane-1-phosphonic dichloride was obtained, bp/0.04: 83°. Cl-(by half-hydrolysis): 11.23%. Calc. for C5H6Cl5O2P: 11.01%. In the absence of triethylammonium chloride, 3.7 g adduct was obtained.

Provenance & Evidence