Triethylamine → HCID 131718071, compound

Participants

Reaction Steps

10 ml of a methylene chloride solution containing 10.0 g of chloroacetylmandelic acid chloride was dropped into a solution of 10.0 g of phytol and 4.5 g of triethylamine dissolved in 30 ml of methylene chloride at 30°-40° C. The resulting mixture was stirred for 2 hours at the same temperature. After the completion of the reaction, the reaction mixture was washed with dilute hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order. The solvent was removed by distillation under reduced pressure. The residue obtained was dissolved in 50 ml of methanol. Thereto were added 3.8 g of triethylamine and 2.9 g of thiourea at room temperature. The resulting mixture was stirred for 3 hours at the same temperature. After the completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue obtained was dissolved in ethyl acetate and the resulting solution was washed with dilute hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant; n-hexane:ethyl acetate=9:1) to obtain 13.0 g (yield: 90%) of oily phytyl mandelate.

Provenance & Evidence