1,2-Dichloroethane → Carbonic acid, chloromethyl phenyl ester

Participants

Reaction Conditions

Reaction Steps

Phenyl chloroformate (9.0 g, 57.5 mmol) was dissolved in 1,2-dichloroethane (50 ml) and pyridine (0.22 g, 2.8 mmol) was added dropwise to the stirred solution. In another reactor, paraformaldehyde (7.0 g, 233.1 mmol) was heated with a heat gun to generate the gaseous monomer. The formaldehyde gas was bubbled into the first reactor through a tube with the outlet below the surface of the liquid. Stirred at 65° C. for 3 hours. Washed three times with water, dried (MgSO4) and concentrated. Distillation (Bp. 64°-67° C. 5×10-4 mbar) yielded 2.7 g product. The product was further purified by flash chromatography (Silikagel 60, petroleum ether/ethyl acetate 95: 5). Yield: 2.1 g. 1H-NMR (CDCl3): delta=5.78 (CH2); 7.18-7.41 ppm (phenyl).

Provenance & Evidence