Benzoic Acid → HCID 57280076, compound

Participants

Reaction Steps

That is, 1.23 g of (2S,5S)-5-butoxy-2-hexanol, 0.86 g of benzoic acid and 2.78 g of triphenylphosphine were dissolved in 25 ml of dry ether. Thereto was dropwise added 2.29 g of diethyl azodicarboxylate (DEAD) at room temperature with stirring. The mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluting solvent: dichloromethane) to obtain 1.56 g of (2R,5S)-5-butoxy-2-hexyl benzoate as a colorless oily substance. 1.56 g of the product was dissolved in 20 ml of methanol. Thereto was dropwise added 516 ml of a 1 N methanol solution of sodium hydroxide at room temperature with stirring. The mixture was stirred for 8 hours at room temperature. The reaction mixture was mixed with 15 ml of water and stirred for 8 hours. To the resulting reaction mixture was added water. Then, extraction with dichloromethane was effected. The extract was dried and concentrated. The residue was subjected to Kugel-rohr distillation under reduced pressure to obtain 0.57 g of the title compound as a colorless oil.

Provenance & Evidence