Pyridine → Cyclohexyl 2-(p-prenylphenyl)propionate

Participants

Reaction Steps

To an ice-cooled solution of 26.0 g of 2-(p-prenylphenyl)propionic acid in 200 ml of benzene were added dropwise 15.7 g of thionyl chloride and 10.4 g of pyridine at the same time with stirring over one hour, and then the mixture was stirred at room temperature for 30 minutes. After ice-cooling, to this mixture were added 13.0 g of cyclohexanol and 10.4 g of pyridine. The resulting mixture was stirred for 2 hours at room temperature, and then washed with 1 N hydrochloric acid, water, 5% aqueous sodium hydroxide and water successively, and dried over anhydrous mangesium sulfate. The solvent was evaporated to give 23.5 g of cyclohexyl 2-(p-prenylphenyl)propionate. b.p. 142° C./0.06 mmHg, IR νmaxneat ; 1730 cm-1.

Provenance & Evidence