N-methyl-2-pyrrolidone → 4Isononyloxycinnamic acid methyl ester

Participants

Reaction Steps

Methanol was removed by distillation from a mixture of 14.2 g (79.7 mmol) 4-hydroxycinnamic acid methyl ester, 150 ml N-methylpyrrolidone and 14.4 g (79.7 mmol) 30% sodium methylate solution in methanol, then 0.5 g tetrabutylammonium chloride and 15.5 g (95.6 mmol) isononyl chloride were added. The addition was followed by heating with stirring for 8 hours to 160 C. After cooling to room temperature, the solution was filtered off from the sodium chloride formed, concentrated to dryness under reduced pressure, the evaporation residue taken up in methylene chloride, washed with water, dried with sodium sulfate and, after concentration by evaporation, chromatographed on silica gel (Merck) (eluent: methylene chloride/toluene =8.2). 20.1 g (91% of the theoretical) 4isononyloxycinnamic acid methyl ester were obtained in the form of a colorless oil having a refractive index at 20 C of 1.5414.

Provenance & Evidence