Methylparaben → HCID 53799950, compound

Participants

Reaction Conditions

Reaction Steps

After removal of the methanol by distillation from a mixture of 20.0 g (131 mmol) 4-hydroxybenzoic acid methyl ester, 200 ml N-methylpyrrolidone, and 25.9 g (144 mmol) 30% sodium methylate solution in methanol, 1.1 g tetrabutylammonium iodide and 38.0 g (158 mmol) farnesyl chloride were added. This was followed by heating with stirring for 7 hours at 160° C. After cooling to room temperature, the solution was filtered off from the sodium chloride formed, evaporated under reduced pressure to dryness, the evaporation residue was taken up in methylene chloride, washed with water, dried with sodium sulfate, distilled under reduced pressure after concentration by evaporation and the fraction boiling at 190° to 202° C. under 0.015 mbar pressure was chromatographed on silica gel (Merck) (eluent: methylene chloride/toluene =7:3). 19.2 g (41% of the theoretical) of 4-farnesyloxybenzoic acid methyl ester was obtained in the form of a colorless oil having a refractive index at 20° C. of 1.5293.

Provenance & Evidence