Hydrochloric Acid → Ethyl 5-(chloromethyl)-2-furancarboxylate

Participants

Reaction Steps

To a solution of 100 g (0.71 M) of ethyl 2-furoate in 250 ml of dichloromethane are added 30.6 g (1.02 M) of paraformaldehyde and 25.4 g (0.19 M) of zinc chloride. Gaseous hydrogen chloride is passed into the reaction medium. An exothermic reaction is observed, and the temperature reaches 35° C. The evolution of gas is maintained up to the end of the reaction, which is monitored by thin-layer chromatography (TLC). The product obtained is then purified by chromatography on silica using dichloromethane as eluent, to give 134.6 g of ethyl 5-chloromethylfuran-2-carboxylate in the form of a colourless oil.

Provenance & Evidence