Furfural → HCID 54135160, compound

Participants

Reaction Steps

To a cooled solution of dimsyl sodium (prepared by heating 4.35 g. of 50% oil dispersion of sodium hydride in 50 ml. dimethylsulfoxide at 60° for 2 hours under argon) is added dropwise 20.0 g. of (4-carboxybutyl)triphenylphosphonium bromide in 90 ml. dimethylsulfoxide. After the solution has stirred at room temperature for one hour, a solution of 4.34 g. furfural in 20 ml. dimethylsulfoxide is added dropwise to the cool (15°) solution over 20 minutes. After 2 hours the dimethylsulfoxide is evaporated, the residue is dissolved in 100 ml. water, filtered and extracted four times with 150 ml. portions of ethyl acetate. The aqueous solution is acidified to pH 1 with 1 N hydrochloric acid, saturated with sodium chloride and extracted twice with 150 ml. portions of ethyl ether. The ether is dried and evaporated to yield the title compound as a yellow oil.

Provenance & Evidence