Chloride → HCID 66769688, compound

Participants

Reaction Steps

Di-n-hexyl 1,3-adamantanedicarboxylate is prepared by way of the following procedure: (A) A 100 mL round bottom flask equipped with a magnetic stir bar is charged with 1,3-admantanedicarboxylic acid (10.0 g, 44.6 mmol) and thionyl chloride (14.5 mL, 0.20 mole). The mixture is refluxed under nitrogen for 4 hrs and cooled to room temperature. Excess thionyl chloride is removed under vacuum and the solid chloride is used for the next step without further purification. (B) A 50 mL round bottom flask equipped with magnetic stirrer is charge with 1-octanol (5.2 g, 40.0 mmol), pyridine (3.24 mL, 40.0 mmol) in 50 mL of methylene chloride. The flask is cooled to 0° C. in ice-water bath, and 1,3-admantanedicarboxyl chloride (5.22 g, 20.0 mmol) in 10 mL of methylene chloride is added dropwise. The reaction mixture is stirred overnight at room temperature. The solvent is removed under vacuum and the residue is dissolved in 60 ml of ether, and filtered to remove solid. The filtrate is concentrated and purified with flash column chromatography to give pure product.

Provenance & Evidence