Triethylamine → Benzoic acid, 4-(phenylmethoxy)-, 1-(trifluoromethyl)heptyl ester

Participants

Reaction Steps

In 20 ml of methylene chloride was dissolved 1.0 g of 4-benzyloxybenzoic acid chloride, and a solution of 0.67 g of optically active 1,1,1-trifluoro-2-octanol, 0.36 g of triethylamine, and a catalytic amount of dimethylaminopyridine in 10 ml of methylene chloride was slowly added thereto under ice-cooling. The reaction mixture was allowed to warm to room temperature, stirred at that temperature for 12 hours, poured into ice-water and extracted with methylene chloride. The methylene chloride phase was washed successively with diluted hydrochloric acid, water, an aqueous 1N sodium carbonate solution, and water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using silica gel to obtain 0.65 g of 1,1,1-trifluoro-2-octyl 4-benzyloxybenzoate.

Provenance & Evidence